GB1192625A - Substituted Phenylacetonitriles - Google Patents
Substituted PhenylacetonitrilesInfo
- Publication number
- GB1192625A GB1192625A GB2660067A GB2660067A GB1192625A GB 1192625 A GB1192625 A GB 1192625A GB 2660067 A GB2660067 A GB 2660067A GB 2660067 A GB2660067 A GB 2660067A GB 1192625 A GB1192625 A GB 1192625A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- group
- prepared
- low
- 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
Links
- 150000007962 benzene acetonitriles Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 230000005494 condensation Effects 0.000 abstract 4
- 238000009833 condensation Methods 0.000 abstract 4
- -1 methylenedioxy group Chemical group 0.000 abstract 3
- 230000002829 reductive effect Effects 0.000 abstract 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000003975 aryl alkyl amines Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 abstract 1
- MUIYVHDFAMWHHP-UHFFFAOYSA-N 2,3-bis(4-chlorophenyl)propanenitrile Chemical compound C1=CC(Cl)=CC=C1CC(C#N)C1=CC=C(Cl)C=C1 MUIYVHDFAMWHHP-UHFFFAOYSA-N 0.000 abstract 1
- NFXAXMOAVPLEBH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC=C(C(C#N)C(C)C)C=C1OC NFXAXMOAVPLEBH-UHFFFAOYSA-N 0.000 abstract 1
- JEWNWPQUVGAWIP-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[(4-chlorophenyl)methyl]-5-oxopentanenitrile Chemical compound ClC1=CC=C(C=C1)C(CCC=O)(CC1=CC=C(C=C1)Cl)C#N JEWNWPQUVGAWIP-UHFFFAOYSA-N 0.000 abstract 1
- JTIHSSVKTWPPHI-UHFFFAOYSA-N 2-amino-2-phenylacetonitrile Chemical compound N#CC(N)C1=CC=CC=C1 JTIHSSVKTWPPHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N n-hexyl alcohol Natural products CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,192,625. Substituted phenylacetonitriles. KNOLL A.G. CHEMISCHE FABRIKEN. 8 June, 1967, No. 26600/67. Heading C2C. Novel compounds of formula wherein A, B, C, A<SP>1</SP>, B<SP>1</SP> and C<SP>1</SP> each represent hydrogen or a halogen atom, or a low-molecular alkyl or alkoxy group or two adjacent groups may together form a methylenedioxy group, Y is a straight or branched chain alkylene group of 1 to 8 carbons in the main chain, Z is a straight or branched chain low-molecular alkylene group of 1 to 8 carbons in the main chain and at least Y or Z is branched chain, R is a low-molecular alkyl group, R 1 is a lowmolecular alkyl group or a saturated or unsaturated cyclic or bicyclic hydrocarbon radical or a group of formula wherein A<SP>11</SP>, B<SP>11</SP> and C<SP>11</SP> each represents H or a halogen atom, or a low-molecular alkyl or alkoxy group or two adjacent groups may together form a methylenedioxy group and n is 0 or 1 and the term low-molecular indicates groups which contain up to 8 carbon atoms, are prepared by one of the following methods in which the symbols have the above meaning and X denotes a reactive acid radical (a) by reaction of a compound of formula with a compound of Formula III or (b) a compound of formula is reacted with a compound of formula R 1 -X, or (c) by reaction of a compound of formula with a compound of Formula III above and then with a compound of formula R 1 X, or (d) a compound of formula is reacted with a compound of formula or (e) by alkylation of the amine of Formula VIII Secondary amines of the Formula VIII above are prepared by reacting a primary arylalkylamine with a #-halogenophenylacetonitrile or by reductive condensation of an arylalkylamine with a carbonyl compound of the phenylacetonitrile, or by reductive condensation of a primary aminophenylacetonitrile with an alkylarylketo compound. α - Isopropyl - α - (3 - chloropropyl) - veratryl cyanide is prepared by condensation of α-isopropyl-veratrylcyanide and 1,3-chlorobromopropane with sodium amide. 5 - Methyl - 4 - cyano - 4 - (31,41 - dimethoxyphenol-1-aminohexane is prepared by the reductive condensation of 5-methyl-4-cyano-4- (3<SP>1</SP>,4<SP>1</SP> - dimethoxyphenyl) - hexanol with hydrazine hydrate and aluminium amalgam. 4,5 - Di - (4 - chlorophenyl) - 4 - cyano - pentanaldehyde is prepared by hydrolysing the corresponding diethyl acetal obtainable by reacting α - (4 - chlorobenzyl) - 4 - chlorobenzyl cyanide with chloropropanol diethyl acetal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2660067A GB1192625A (en) | 1967-06-08 | 1967-06-08 | Substituted Phenylacetonitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2660067A GB1192625A (en) | 1967-06-08 | 1967-06-08 | Substituted Phenylacetonitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1192625A true GB1192625A (en) | 1970-05-20 |
Family
ID=10246165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2660067A Expired GB1192625A (en) | 1967-06-08 | 1967-06-08 | Substituted Phenylacetonitriles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1192625A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62190155A (en) * | 1986-01-31 | 1987-08-20 | バスフ アクチェン ゲゼルシャフト | Basically substituted phenylacetonitrile and medicine |
| US5643947A (en) * | 1989-12-21 | 1997-07-01 | G. D. Searle & Co. | ω-amino-α-phenylalkanonitrile derivatives |
-
1967
- 1967-06-08 GB GB2660067A patent/GB1192625A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62190155A (en) * | 1986-01-31 | 1987-08-20 | バスフ アクチェン ゲゼルシャフト | Basically substituted phenylacetonitrile and medicine |
| US5643947A (en) * | 1989-12-21 | 1997-07-01 | G. D. Searle & Co. | ω-amino-α-phenylalkanonitrile derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |