US2647815A - Alkyl diformyl phenylenediamines - Google Patents
Alkyl diformyl phenylenediamines Download PDFInfo
- Publication number
- US2647815A US2647815A US224444A US22444451A US2647815A US 2647815 A US2647815 A US 2647815A US 224444 A US224444 A US 224444A US 22444451 A US22444451 A US 22444451A US 2647815 A US2647815 A US 2647815A
- Authority
- US
- United States
- Prior art keywords
- diformyl
- methyl
- phenylenediamine
- alkyl
- ethyl
- 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
- -1 Alkyl diformyl phenylenediamines Chemical class 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- KDLCQMBNDVZRKM-UHFFFAOYSA-N n-(4-formamidophenyl)formamide Chemical compound O=CNC1=CC=C(NC=O)C=C1 KDLCQMBNDVZRKM-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- UQBNGMRDYGPUOO-UHFFFAOYSA-N 1-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CNC1=CC=CC(NC)=C1 UQBNGMRDYGPUOO-UHFFFAOYSA-N 0.000 description 1
- ZEMODTUZIWTRPF-UHFFFAOYSA-N 1-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(NCC)C=C1 ZEMODTUZIWTRPF-UHFFFAOYSA-N 0.000 description 1
- PVRZMTHMPKVOBP-UHFFFAOYSA-N 1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CNC1=CC=C(NC)C=C1 PVRZMTHMPKVOBP-UHFFFAOYSA-N 0.000 description 1
- WLAWDMHLJNVGSV-UHFFFAOYSA-N 3-n-ethylbenzene-1,3-diamine Chemical compound CCNC1=CC=CC(N)=C1 WLAWDMHLJNVGSV-UHFFFAOYSA-N 0.000 description 1
- SKIBELYSXFYZPS-UHFFFAOYSA-N 4-n-ethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(N)C=C1 SKIBELYSXFYZPS-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- CFFWXRUMZWINGY-UHFFFAOYSA-N N-(4-ethylphenyl)nitramide Chemical compound [N+](=O)([O-])NC1=CC=C(C=C1)CC CFFWXRUMZWINGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004048 vat dyeing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6497—Amides of di- or polyamines; Acylated polyamines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
- D06P1/28—Esters of vat dyestuffs
Definitions
- This invention relates to a, new group of compounds which are alkyl diformyl phenylenediamines and to a method for their preparation;
- R is RNCHO 1 selected from the group conslstmg of alkyl, hy-
- NHR N-OHO N-OHO Formylation may be accomplished in either case by refluxing with formic acid alone or in the presence of an-agent.to remove the water formed azeotropi'cally.-; Toluene, xylene or chlorobenzene are suitable agents. The latter is the preferred method.
- the new compounds are useful in solubilizing sulfuric esters of vat dyestuffs in aqueous mediums, particularly aqueous printing paste formulations.
- This property of the instant commajor problems one is faced with in vat dyeing is to produce a uniform, level, non-specky dyed product amo,effectlthis it is necessary to have the dyestufi irr as fine a state of sub-division as possible and preferably in solution.
- the new compounds of this invention enhance the solubility of the sulfuric acid esters of vat dyestuffs in aqueous mediums thereby leading to level, non-specky dyeings,
- EXAMPLE 5 Mixture of (a) N,N-dimethyl, N,N-diformylp-phenylenediamine, ('b) N,N'-diethyl, N,N'-diformyl-p-phenylenediamine and (c) N-methyl, N'-ethyl, N,N'-diformyl-p-phenylenediamine.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Aug. *4, 1953 ALKYL DIFORMYL PHENYLENEDIAMINES- Saul R. Bue and Samuel A. Glicl iman, Easton, Pa., assigno'rs to General Aniline& Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application May 3, 1951, Serial No. 224,444
6 Claims.
This invention relates to a, new group of compounds which are alkyl diformyl phenylenediamines and to a method for their preparation;
More particularly, it relates to compounds having the following general formula:
wherein Rdsselected from the group consisting of 'alkyl (methyl, ethyl, propyl, ,butyl) and hy-r droxy alkyl (hydroxy methyl, hydroxy ethyl, hy-
5 droxy propy1,'hydroxy butyl), and wherein R is RNCHO 1 selected from the group conslstmg of alkyl, hy-
droxy alkyl and hydrogen. 10 The don nounds prepared are summarized in. R'-NCHO the following table:
M. P. or Other Name Formula Physical Property N,N-Diformyl-N-methyl-p-phen- CH: CHO 138-141.
ylenediamine. \N/
"NHCHO NN'-Dilormyl-N-ethyl-phen 1- 4 0,11 CHO 79-81.
enediamlne. p y
NHCHO N ,N'-p-P henylene bis-N-methylon em 210-212.
formamide. v v. 0011 -\CHO N,N-m-Phenylenebis-N-methyl- CH1 148-150. tormamlde. I
CH0 CH1 V Y c110 NN!-li1' rmyl-N-2 hydroxyethyl- 110633011, oil.
ia-phenylenediamine.
V /N NHOHO 1. OCH N,N'-m-Phenyle11ebis-N- ethyl- 0,115 M, P.. 4547. formamide.. N/ B.P.182-'4/0.4mm
CH0 /CH0 N\" 4 01H;
Name
M. P. or Other Physical Property N ,N'-Diformyl N-methyl-m-phen I ylenediamine.
N,Nl Diformyl, N methyl N ethyl-p-phenylenediamlne.-
N,N Diformyl, N methyl N C 1H5 ethyl-m-phenylenediamine. l
N-CHO III-CHO 0 HI oll notldistillablal- Also, mixtures of the above, prepared eitherby mixing of the pure compoundsior by synthesis from mixtures of intermediates. These compounds were prepared inrtwo different ways:
(1) By formylation of" the corresponding mono-formyl derivatives:
\ a /N NH; H0003 OCH OCH
(2) By diformylation of the correspondinadi i 65""poundscls1'eXtremely valuable since one of the amines:
NHR N-OHO N-OHO Formylation may be accomplished in either case by refluxing with formic acid alone or in the presence of an-agent.to remove the water formed azeotropi'cally.-; Toluene, xylene or chlorobenzene are suitable agents. The latter is the preferred method.
'Iliet.follo.wing..- examples illustrate preferred embddirhentseofthe' invention, but variations and substitutions may be made within the scope of the claims.
The new compounds are useful in solubilizing sulfuric esters of vat dyestuffs in aqueous mediums, particularly aqueous printing paste formulations. This property of the instant commajor problems one is faced with in vat dyeing is to produce a uniform, level, non-specky dyed product amo,effectlthis it is necessary to have the dyestufi irr as fine a state of sub-division as possible and preferably in solution. The new compounds of this invention enhance the solubility of the sulfuric acid esters of vat dyestuffs in aqueous mediums thereby leading to level, non-specky dyeings,
5., EXAMPLE 1- N,N-difo1mg Z-N-methyl-p-phenylenediamine HCOOH CHO H c NHON/ A crude sample of N-methyl, N-formyl-pphenylenediamine, prepared by the catalytic reduction of 88 parts of the corresponding nitrocompound, was treated with 100 parts of 99% formic acid and refluxed three hours. The water and excess formic acid were removed in vacuo, and the product crystallized on scratching. M. P. 138-141 C.
CHO
EXAMPLE 2 N,N-diformyZ-N-ethyZ-p-phenylenediamine NG-NHOHO OCH 70.0 parts of p-ethyl nitroaniline is hydrogenated in 140 parts of 99% formic acid over a platinum catalyst. The catalyst is filtered and 500 parts toluene added to the mixture. Reflux through a fractionating column in such a manner that the toluene is continuously returned to the pot and the lower water formic acid layer is distilled. When the boiling point of toluene was reached the toluene was removed in vacuo and the residue crystallized. M. P. 79-81 C.
EXAIWPLE 3 N,N-dimethyl, N,N'-diformyZ-m-phenylenedz'amine A crude sample of N,N'-dimethyl-m-phenylenediamine, prepared by the Biichner reaction on 110 parts of resorcinol, was formylated with 200 parts, 90% formic acid and 500 parts toluene by the procedure described in Example 2. On removal of the solvents there was obtained 141 parts (73% yield based on resorcinol) of the desired product. M. P. 148-150 0.
EXAMPLE 4 NJW-dz'ethyl, N,N'-di,formyZ-p-phenylenediamine A sample of N,N'-diethy1-p-phenylenediamine prepared by the Biichner reaction between hydroquinone and ethylamine was formylated as in Example 3. The product was isolated in the same way and melted at 126-129 C.
EXAMPLE 5 Mixture of (a) N,N-dimethyl, N,N-diformylp-phenylenediamine, ('b) N,N'-diethyl, N,N'-diformyl-p-phenylenediamine and (c) N-methyl, N'-ethyl, N,N'-diformyl-p-phenylenediamine.
A mixture of N,N'-dimethyl-p-phenylenediamine, N,N'-diethyl-p-phenylenediamine and N methyl, N-ethyl-p-phenylenediamine containing methyl to ethyl groups in the ratio of one to 6. three was .formyla'ted as-in Example -3. The productmelted at 96--150 q.
EXAIVIPLE 6 Identicalwith Example 5, but with methyl to ethyl groups in-the ratio of one t nine. The
product melted at: u v 1 'PLE Mixture of meta isomers prepared as in Example 5. Ratio of methyl to ethyl groups 9 to l. M. P. of product 146-149.
We claim: 1 A compound having the general formula:
R-NCHO R' NCHO wherein the relative position of the two substituted amino groups is selected from the class consisting of mand p-, R is selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and hydroxyalkyl radicals of 2 to 4 carbon atoms, and R is selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and hydroxyalkyl radicals of 2 to 4 carbon atoms and hydrogen.
2. A compound having the formula:
5. A compound having the formula:
6. A mixture of N,N-dimethy1, N,N-diformylp phenylenediamine; N,N' diethyl, N,N' diformyl-p-phenylenediamine; and N-methyl, N- ethyl, N,N' diformyl p phenylenediamine; wherein the methyl and ethyl groups are in the ratio of 1 :3.
SAUL R. BUC.
SAMUEL A. GLICKMAN.
(References on following page)
Claims (1)
- 6. A MIXTURE OF N,N''-DIETHYL, N,N''-DIFORMYLP-PHENYLENDIAMINE; N,N''-DIETHYL, N,N''-DIFORMYL-P-PHENYLENDDIAMINE; AND N-METHYL, N''ETHYL, N,N''-DIFORMLY-P-PHENYLENEDIAMINE; WHEREIN THE METHYL AND ETHYL GROUPS ARE IN THE RATIO OF 1:3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US224444A US2647815A (en) | 1951-05-03 | 1951-05-03 | Alkyl diformyl phenylenediamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US224444A US2647815A (en) | 1951-05-03 | 1951-05-03 | Alkyl diformyl phenylenediamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2647815A true US2647815A (en) | 1953-08-04 |
Family
ID=22840711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US224444A Expired - Lifetime US2647815A (en) | 1951-05-03 | 1951-05-03 | Alkyl diformyl phenylenediamines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2647815A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953423A (en) * | 1957-01-29 | 1960-09-20 | Gen Aniline & Film Corp | Solubilization of dissociable ionic structures |
| US3937729A (en) * | 1971-09-15 | 1976-02-10 | Stauffer Chemical Company | Meta-bis anilide derivatives and their utility as herbicides |
| US4555363A (en) * | 1983-01-21 | 1985-11-26 | Beecham Group P.L.C. | Process for the preparation of β-lactam compounds |
| US5536876A (en) * | 1992-06-13 | 1996-07-16 | Basf Aktiengesellschaft | Formylamino-aminophenol compounds and their use in preparation of fiber-reactive formazan dyes |
| WO2004074234A1 (en) * | 2003-02-20 | 2004-09-02 | Lonza Ag | Process for the preparation of n-substituted formamides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1273901A (en) * | 1917-01-31 | 1918-07-30 | Gilbert Thomas Morgan | Process for the manufacture of para-amino-n-methylformanilid. |
-
1951
- 1951-05-03 US US224444A patent/US2647815A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1273901A (en) * | 1917-01-31 | 1918-07-30 | Gilbert Thomas Morgan | Process for the manufacture of para-amino-n-methylformanilid. |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953423A (en) * | 1957-01-29 | 1960-09-20 | Gen Aniline & Film Corp | Solubilization of dissociable ionic structures |
| US3937729A (en) * | 1971-09-15 | 1976-02-10 | Stauffer Chemical Company | Meta-bis anilide derivatives and their utility as herbicides |
| US4555363A (en) * | 1983-01-21 | 1985-11-26 | Beecham Group P.L.C. | Process for the preparation of β-lactam compounds |
| US5536876A (en) * | 1992-06-13 | 1996-07-16 | Basf Aktiengesellschaft | Formylamino-aminophenol compounds and their use in preparation of fiber-reactive formazan dyes |
| WO2004074234A1 (en) * | 2003-02-20 | 2004-09-02 | Lonza Ag | Process for the preparation of n-substituted formamides |
| JP2006519201A (en) * | 2003-02-20 | 2006-08-24 | ロンザ ア−ゲ− | Process for producing N-substituted formamide |
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