Water → HCID 57228633, compound

HRID 978886Notes

Reaction equation

HRID 978886 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 acid 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 drying 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
  4. dry with materialby drying over phosphorus pentachloride

Sources & evidence

ORD record
ord-da7c861a113e4d8a9cf5fe2827f57a7d
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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