US2884448A - Hydrolysis of n-substituted amides - Google Patents
Hydrolysis of n-substituted amides Download PDFInfo
- Publication number
- US2884448A US2884448A US595139A US59513956A US2884448A US 2884448 A US2884448 A US 2884448A US 595139 A US595139 A US 595139A US 59513956 A US59513956 A US 59513956A US 2884448 A US2884448 A US 2884448A
- Authority
- US
- United States
- Prior art keywords
- acenaphthene
- acid
- carboxanilide
- hydrolysis
- excess
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000007062 hydrolysis Effects 0.000 title description 9
- 238000006460 hydrolysis reaction Methods 0.000 title description 9
- 150000001408 amides Chemical class 0.000 title description 3
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 26
- -1 N-SUBSTITUTED AMIDE Chemical class 0.000 claims description 18
- OMLGHGJYBKVAAR-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-1-carboxylic acid Chemical class C1=CC(C(C(=O)O)C2)=C3C2=CC=CC3=C1 OMLGHGJYBKVAAR-UHFFFAOYSA-N 0.000 claims description 13
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims description 13
- 239000003599 detergent Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- DXKAWGBIIVQFIE-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-5-carboxylic acid Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C(=O)O DXKAWGBIIVQFIE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical class CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
Definitions
- This invention relates to the hydrolysis of N-substituted amides of acenaphthene carboxylic acids and relates-more particularly to the hydrolysis of acenaphthene 'carboxanilides to produce their corresponding acids.
- Another object of this invention is the provision of an improved process for hydrolyzing acenaphthene carboxanilides to their corresponding acids by the use of an aqueous hydrolytic medium containing a surface active agent and an excess of alkali.
- the process of the instant invention may be employed in the hydrolysis of any N-substituted amide of acenaphthene carboxylic acid.
- this invention will be particularly described in connection with the hydrolysis of acenaphthene S-carboxanilide and acenaphthene 5,6- carboxanilide to their corresponding acids, namely 5- acenaphthoic acid and 5,6-acenaphthalic acid, respectively, since these are valuable intermediates for dyestuffs, fluorescing agents and pharmaceuticals.
- 5,6-acenaphthalic acid may be oxidized in substantially quantitative yield to 1,4,5,8-tetracarboxylic acid (Tetra Acid) which is useful in the preparation of vat dyes such as Indanthrene Brilliant Orange GR, Indanthrene Scarlet GG, Indanthrene Bordeaux RR and the like.
- Tetra Acid 1,4,5,8-tetracarboxylic acid
- the N-substituted amide such as acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide
- the N-substituted amide are hydrolyzed by suspending the amide in water containing a slight excess of caustic and a trace of wetting agent or detergent, and the suspension heated under superatmospheric pressure for 4 to 6 hours at a temperature of about 200 C.
- the solution obtained is treated with a suitable acid, such as hydrochloric acid or sulfuric acid, for example, to produce the corresponding organic acid.
- a few steel balls may be added to the suspension for the purpose of breaking up any lumps therein and thus facilitating hydrolysis.
- any suitable alkaliand heat-stable wetting agent or detergent may be employed in the process of the instant invention such as, for example, the dioctyl ester of wifesuccinic acid (Aerosol OT), alkyl benzene sulfonates, e.g. dodecyl benzene sulfonates, Igepon T types (N-acyl- N-methyl-taurines), Igepal types (polyoxyethylated alkyl "ice phenols), long chain alcohol sulfates and Alipals (sulfated polyoxyethylated alkyl phenols).
- the dioctyl ester of wifesuccinic acid (Aerosol OT)
- alkyl benzene sulfonates e.g. dodecyl benzene sulfonates
- Igepon T types N-acyl- N-methyl-taurines
- Igepal types polyoxyeth
- Example I drying gave a quantitative yield of pure white S-acenaphthoic acid.
- Example II A mixture of 156 grams of acenaphthene 5,6-dicarbanilide, 58 grams of potassium hydroxide, 1 gram of Aerosol OT and 600 cc. of water, to which were added a few %-inch steel balls, was shaken in a steel bomb for 6 hours at 200 C. The dark-brown solution obtained was adjusted to approximately pH 7 With dilute hydrochloric acid, charcoaled and filtered. Acidification, filtering, washing and drying gave an almost quantitative yield of nearly white 5,6-acenaphthalic acid.
- Process for preparing acenaphthene carboxylic acids which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic and a small amount of alkaliand heatstable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution.
- Process for preparing acenaphthene carboxylic acids which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene 5- carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic and a small amount of alkaliand heatstable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution by adding thereto a mineral acid so as to cause acenaphthene carboxylic acid to precipitate.
- an N-substituted amide of acenaphthene carboxylic acid selected from the group consisting of acenaphthene 5- carboxanilide and acenaphthene 5,6-carboxanilide
- Process for preparing acenaphthene carboxylic acids which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic, selected from the group consisting of sodium hydroxide and potassium hydroxide, and a small amount of alkaliand heat-stable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution by adding thereto a mineral acid so as to cause acenaphthene carboxylic acid to precipitate.
- an N-substituted amide of acenaphthene carboxylic acid selected from the group consisting of acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide
- Process for preparing S-acenaphthoic acid which comprises forming a mixture of acenaphthene S-carboxanilide, an excess of sodium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation for 4 hours at 200 C., and precipitating S-acenaphthoic acid from the resulting solution by adding hydrochloric acid to said solution.
- Process for preparing 5,6-acenaphthalic acid which comprises forming a mixture of acenaphthene 5,6-dicarboxanilide, an excess of potassium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation for 6 hours at 200 C., and precipitating 5,6-acenaphthalic acid from the resulting solution by adding hydrochloric acid to said solution.
- Process for preparing S-acenaphthoic acid which comprises forming a mixture of acenaphthene S-carboxanilide, an excess of sodium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation in the presence of steel balls for 4 hours at 200 C., and precipitating S-acenaphthoic acid from the resulting solution by adding hydrochloric acid to said solution.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent HYDROLYSIS F N-SUBSTITUTED AMIDES William L. Moshy, North "Plainfield, and Saul R. Buc,
Easton, N.J., assignors toGenerzrl Aniline & Film CorporatiomNew York, N.Y., a corporation of Delaware No Drawing. Application July 2, 1956 Serial No. 595,139
7 Claims. (Cl-.260-515) This invention relates to the hydrolysis of N-substituted amides of acenaphthene carboxylic acids and relates-more particularly to the hydrolysis of acenaphthene 'carboxanilides to produce their corresponding acids.
Heretofore, in the hydrolysis of N-substituted amides of acenaphthene carboxylic acids the hydrolytic medium employed comprised ethylene glycol and potassium hydroxide. However, the results obtained by the use of this hydrolytic medium were not satisfactory as to yield or purity. The amount of final product obtained fell 1213% short of quantitative yield and was quite impure. It is, accordingly, an important object of this invention to provide a novel process for the hydrolysis of acenaphthene carboxanilides to their corresponding acids wherein improved yield and quality of product is obtained.
Another object of this invention is the provision of an improved process for hydrolyzing acenaphthene carboxanilides to their corresponding acids by the use of an aqueous hydrolytic medium containing a surface active agent and an excess of alkali.
Other objects of this invention will appear from the following detailed description and claims.
The process of the instant invention may be employed in the hydrolysis of any N-substituted amide of acenaphthene carboxylic acid. However, this invention will be particularly described in connection with the hydrolysis of acenaphthene S-carboxanilide and acenaphthene 5,6- carboxanilide to their corresponding acids, namely 5- acenaphthoic acid and 5,6-acenaphthalic acid, respectively, since these are valuable intermediates for dyestuffs, fluorescing agents and pharmaceuticals. For example, 5,6-acenaphthalic acid may be oxidized in substantially quantitative yield to 1,4,5,8-tetracarboxylic acid (Tetra Acid) which is useful in the preparation of vat dyes such as Indanthrene Brilliant Orange GR, Indanthrene Scarlet GG, Indanthrene Bordeaux RR and the like.
In accordance with this invention, the N-substituted amide, such as acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide, are hydrolyzed by suspending the amide in water containing a slight excess of caustic and a trace of wetting agent or detergent, and the suspension heated under superatmospheric pressure for 4 to 6 hours at a temperature of about 200 C. The solution obtained is treated with a suitable acid, such as hydrochloric acid or sulfuric acid, for example, to produce the corresponding organic acid. If desired, a few steel balls may be added to the suspension for the purpose of breaking up any lumps therein and thus facilitating hydrolysis.
Any suitable alkaliand heat-stable wetting agent or detergent may be employed in the process of the instant invention such as, for example, the dioctyl ester of wifesuccinic acid (Aerosol OT), alkyl benzene sulfonates, e.g. dodecyl benzene sulfonates, Igepon T types (N-acyl- N-methyl-taurines), Igepal types (polyoxyethylated alkyl "ice phenols), long chain alcohol sulfates and Alipals (sulfated polyoxyethylated alkyl phenols).
The instant invention will be more clearly understood from the'following examples which are merely illustrative and inno way flimitative.
Example I drying gave a quantitative yield of pure white S-acenaphthoic acid.
Example II A mixture of 156 grams of acenaphthene 5,6-dicarbanilide, 58 grams of potassium hydroxide, 1 gram of Aerosol OT and 600 cc. of water, to which were added a few %-inch steel balls, was shaken in a steel bomb for 6 hours at 200 C. The dark-brown solution obtained was adjusted to approximately pH 7 With dilute hydrochloric acid, charcoaled and filtered. Acidification, filtering, washing and drying gave an almost quantitative yield of nearly white 5,6-acenaphthalic acid.
It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of our invention.
Having described our invention what we desire to secure by Letters Patent is:
1. Process for preparing acenaphthene carboxylic acids, which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic and a small amount of alkaliand heatstable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution.
2. Process for preparing acenaphthene carboxylic acids, which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene 5- carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic and a small amount of alkaliand heatstable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution by adding thereto a mineral acid so as to cause acenaphthene carboxylic acid to precipitate.
3. Process for preparing acenaphthene carboxylic acids, which comprises suspending an N-substituted amide of acenaphthene carboxylic acid, selected from the group consisting of acenaphthene S-carboxanilide and acenaphthene 5,6-carboxanilide, in water containing an excess of caustic, selected from the group consisting of sodium hydroxide and potassium hydroxide, and a small amount of alkaliand heat-stable detergent, heating said suspension at a temperature of about 200 C. for from four to six hours, and acidifying the resulting solution by adding thereto a mineral acid so as to cause acenaphthene carboxylic acid to precipitate.
4. Process for preparing S-acenaphthoic acid, which comprises forming a mixture of acenaphthene S-carboxanilide, an excess of sodium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation for 4 hours at 200 C., and precipitating S-acenaphthoic acid from the resulting solution by adding hydrochloric acid to said solution.
5. Process for preparing 5,6-acenaphthalic acid, which comprises forming a mixture of acenaphthene 5,6-dicarboxanilide, an excess of potassium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation for 6 hours at 200 C., and precipitating 5,6-acenaphthalic acid from the resulting solution by adding hydrochloric acid to said solution.
6. Process for preparing S-acenaphthoic acid, which comprises forming a mixture of acenaphthene S-carboxanilide, an excess of sodium hydroxide, a small amount of alkaliand heat-stable detergent and water, heating said mixture under pressure and with agitation in the presence of steel balls for 4 hours at 200 C., and precipitating S-acenaphthoic acid from the resulting solution by adding hydrochloric acid to said solution.
7. Process for preparing 5,6-acenaphthalic acid, which References Cited in the file of this patent UNITED STATES P TENTS 2,498,656 De Groote et al. Feb. 28, 1950 2,509,245 Nikawitz et a1 May 30, 1950 FOREIGN PATENTS 274,894 Great Britain Feb. 16, 1928 783,091 France July 8, 1935 OTHER REFERENCES Schwartz et 211.: Surface Active Agents, pp. 380, 513-514 (1949), Interscience Publishers.
Claims (1)
1. PROCESS FOR PREPARING ACENAPHTHENE CARBOXYLIC ACIDS, WHICH COMPRISES SUSPENDING AN N-SUBSTITUTED AMIDE OF ACENAPHTHENE CARBOXYLIC ACID, SELECTED FROM THE GROUP CONSISTING OF ACENAPHTHENE 5-CARBOXANILIDE AND ACENAPHTHENE 5,6-CARBOXANILIDE, IN WATER CONTAINING AN EXCESS OF CAUSTIC AND A SMALL AMOUNT OF ALKALI- AND HEATSTABLE DETERGENT, HEATING SAID SUSPENSION AT A TEMPERATURE OF ABOUT 200*C, FOR FROM FOUR TO SIX HOURS, AND ACIDIFYING THE RESULTING SOLUTION.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US595139A US2884448A (en) | 1956-07-02 | 1956-07-02 | Hydrolysis of n-substituted amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US595139A US2884448A (en) | 1956-07-02 | 1956-07-02 | Hydrolysis of n-substituted amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2884448A true US2884448A (en) | 1959-04-28 |
Family
ID=24381898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US595139A Expired - Lifetime US2884448A (en) | 1956-07-02 | 1956-07-02 | Hydrolysis of n-substituted amides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2884448A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011106570A1 (en) * | 2010-02-24 | 2011-09-01 | Medivation Prostate Therapeutics, Inc. | Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB274894A (en) * | 1926-07-24 | 1928-02-16 | Ig Farbenindustrie Ag | Manufacture of carboxylic acids of acenaphthene |
| FR783091A (en) * | 1934-01-05 | 1935-07-08 | Ici Ltd | Manufacturing process of acenaphthene -5-carboxylic and -5: 6-dicarboxylic acids and their anhydrides |
| US2498656A (en) * | 1948-05-29 | 1950-02-28 | Petrolite Corp | Processes for breaking petroleum emulsions |
| US2509245A (en) * | 1947-03-20 | 1950-05-30 | Givaudan Corp | Preparation of 2, 4, 5-trichlorophenol |
-
1956
- 1956-07-02 US US595139A patent/US2884448A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB274894A (en) * | 1926-07-24 | 1928-02-16 | Ig Farbenindustrie Ag | Manufacture of carboxylic acids of acenaphthene |
| FR783091A (en) * | 1934-01-05 | 1935-07-08 | Ici Ltd | Manufacturing process of acenaphthene -5-carboxylic and -5: 6-dicarboxylic acids and their anhydrides |
| US2509245A (en) * | 1947-03-20 | 1950-05-30 | Givaudan Corp | Preparation of 2, 4, 5-trichlorophenol |
| US2498656A (en) * | 1948-05-29 | 1950-02-28 | Petrolite Corp | Processes for breaking petroleum emulsions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011106570A1 (en) * | 2010-02-24 | 2011-09-01 | Medivation Prostate Therapeutics, Inc. | Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
| US9174943B2 (en) | 2010-02-24 | 2015-11-03 | Medivation Prostate Therapeutics, Inc. | Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
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