GB907777A - A process for the preparation of tertiary acid amides - Google Patents
A process for the preparation of tertiary acid amidesInfo
- Publication number
- GB907777A GB907777A GB4116060A GB4116060A GB907777A GB 907777 A GB907777 A GB 907777A GB 4116060 A GB4116060 A GB 4116060A GB 4116060 A GB4116060 A GB 4116060A GB 907777 A GB907777 A GB 907777A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propyl
- linked
- carboxylic acid
- enyl
- prop
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
Abstract
Acid amides in which the nitrogen atom has one valency linked to a carbon, phosphorus or silicon atom, the other two valencies being linked to carbon atoms one of which is linked to a further carbon atom by an olefinic double bond (see Group IV(b)), may be polymerized, copolymerized with other unsaturated compounds, used for modifying the properties of known polymers and copolymers, and used in the preparation of polymeric oil additives. The invention also comprises compounds of the general formula <FORM:0907777/IV(a)/1> wherein alk and R represent alkyl groups which may be the same or different and R1, R11 and R111 are alkyl groups and/or hydrogen. These compounds are prepared by treating an aldimine or ketimine of the general formula R-N=CR1-CHR11R111 wherein R, R1, R11 and R111 are as defined above, with a dialkylamino-trichlorosilane at a temperature of below 30 DEG C. and subsequently splitting of a molecule of hydrogen chloride by heating in the presence of a tertiary amine. Several suitable aldimines are specified and in Example (7) diethylamino-(propyl-prop-1-enylamino)-dichlorosilane is prepared from diethylaminotrichlorosilane and N-propyl-propanaldimine in the presence of triethylamine and benzene. Specification 539,332 is referred to.ALSO:Acid amides in which the nitrogen atom has one valency linked to a carbon, phosphorus or silicon atom (see Group IV(a)), the other two valencies being linked to carbon atoms one of which is linked to a further carbon atom by an olefinic double bond, are prepared by treating an aldimine or ketimine of the general formula R-N = CR1-CHR11R111 wherein R is an alkyl radical and R1, R11 and R111 are hydrogen atoms and/or alkyl groups, with a carboxylic acid anhydride, a carboxylic acid chloride or a phosphorus oxyhalide at a temperature below 30 DEG C. and subsequently splitting off a molecule of the hydrogen halide corresponding to the acid halide used or the carboxylic acid corresponding to the acid anhydride used by heating in the presence of a tertiary amine. The invention also comprises dichlorophosphoric amides of the general formula Cl2.P(O).N(R).C(R1)=CR11R111 R, R1, R11 and R111 being as defined above. The addition of acid halide or carboxylic acid anhydride may also be carried out in the presence of a tertiary amine. The reaction is preferably carried out in the presence of an inert hydrocarbon solvent such as benzene, toluene, xylene or hexane. The reaction is preferably carried out with approximately stoichiometric proportions of the imine and acid halide or carboxylic acid anhydride and a slight excess of tertiary amine. The products may be recovered from the reaction mixture by distillation, any insoluble salts present being optionally filtered off before-hand. Specified tertiary amines are triethylamine and pyridine. Specified starting materials are N - propyl - propanaldimine, N - propyl-acetaldimine and N - propyl - butanaldimine, acetic, propionic and butyric anhydrides, acetyl, propionyl and benzoyl chlorides and phosphorus oxychloride. In examples the following compounds are prepared: (1) N-propyl-N-vinyl-acetamide; (2), (4) and (5) N-propyl-N-prop-1-enyl-acetamide; (3) N-propyl-N-but-1-enyl-acetamide; (6) N-propyl-N-prop-1-enyl-benzamide; (8) propyl-(prop-1-enyl)-amino-phosphoryl dichloride. In Example (3) N-propyl acetamide is formed as a by-product. The products may be used as intermediates in the preparation of insecticides and may be polymerized or co-polymerized (see Group IV(a)). Specification 539,332 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL246020A NL246020A (en) | 1959-12-02 | 1959-12-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB907777A true GB907777A (en) | 1962-10-10 |
Family
ID=19752064
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4116060A Expired GB907777A (en) | 1959-12-02 | 1960-11-30 | A process for the preparation of tertiary acid amides |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1129946B (en) |
GB (1) | GB907777A (en) |
NL (1) | NL246020A (en) |
-
1959
- 1959-12-02 NL NL246020A patent/NL246020A/xx unknown
-
1960
- 1960-11-30 DE DES71492A patent/DE1129946B/en active Pending
- 1960-11-30 GB GB4116060A patent/GB907777A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL246020A (en) | 1964-02-10 |
DE1129946B (en) | 1962-05-24 |
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