Water → HCID 57228633, compound

HRID 2231580Notes

Reaction equation

HRID 2231580 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8](N)[S:9][CH:10]=1)[CH3:2].[Cl:13][CH2:14][C:15](Cl)=[O:16].O.C[N:20](C)C(=O)C>>[CH2:1]([O:3][C:4](=[O:12])[CH:5]([NH:20][C:15](=[O:16])[CH2:14][Cl:13])[C:6]1[N:7]=[CH:8][S:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 31374DimethylacetamideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 57228633HCID 57228633, compoundYield 92%

Procedure

To a solution of 9.3 g of 2-amino-4-thiazolyl acetic aicd ethyl ester in 50 ml of N,N-dimethylacetamide is added under ice-cooling 7.91 g of chloroacetyl chloride with stirring. The mixture is stirred for one hour at room temperature, to which is added 300 ml of water. Then the resulting crystals are collected by filtration. The crystals are washed with water and ether in this order, followed by driving over phosphorus pentachloride to yield 12.1 g (92%) of 2-chloroacetamido-4-thiazolyl-acetic acid ethyl ester, m.p. 145°-146° C.

Workup

  1. stirringThe mixture is stirred for one hour at room temperature, to which
  2. filtrationThen the resulting crystals are collected by filtration
  3. washThe crystals are washed with water and ether in this order

Sources & evidence

ORD record
ord-24ee4154b914437ea58e7a7a33e2d5c7
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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