GB855444A - Method of preparing esters of n-substituted ethylene imine carboxylic acids - Google Patents
Method of preparing esters of n-substituted ethylene imine carboxylic acidsInfo
- Publication number
- GB855444A GB855444A GB21967/57A GB2196757A GB855444A GB 855444 A GB855444 A GB 855444A GB 21967/57 A GB21967/57 A GB 21967/57A GB 2196757 A GB2196757 A GB 2196757A GB 855444 A GB855444 A GB 855444A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- ester
- tertiary base
- ethylene imine
- effected
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
Abstract
Esters of N-substituted ethylene imine carboxylic acids of the general formula: <FORM:0855444/IV(b)/1> wherein R is a triaryl methyl group and R1 is an alkyl group are prepared by inter-reacting an inorganic acid salt of a serine alkyl ester, with a triaryl methyl halide and a tertiary base, condensing the resulting N-triaryl methyl serine ester in the presence of a tertiary base with a sulphonyl halide R11 SO2 X, where X is chlorine or bromine and R11 an alkyl, aryl or aralkyl group, and cyclising the resulting O-R11 sulphonyl-N-triaryl methyl serine ester by means of a basic agent to form the desired ethylene imine carboxylic ester. The first step is preferably effected in an anhydrous solvent at below 10 DEG C., suitable bases being specified. The reaction with the sulphonyl halide for example methyl sulphonyl chloride may be effected in the presence of a tertiary base at below 40 DEG C. The cyclisation may be effected at 10 DEG to 150 DEG C., using as basic agent a tertiary base, an alkali metal alcoholate or an alkali metal salt of a carboxylic acid. The process may be effected with or without isolation of the intermediates and in the latter case, the basic agent for the cyclisation may be provided by using an excess of the tertiary base in the first step. Examples describe the preparation of N-triphenyl methyl ethylene imine carboxylic acid methyl ester.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS855444X | 1956-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB855444A true GB855444A (en) | 1960-11-30 |
Family
ID=5456194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21967/57A Expired GB855444A (en) | 1956-08-03 | 1957-07-11 | Method of preparing esters of n-substituted ethylene imine carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB855444A (en) |
-
1957
- 1957-07-11 GB GB21967/57A patent/GB855444A/en not_active Expired
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