Water → Ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate

HRID 27267Notes

Reaction equation

HRID 27267 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:10][O:11][CH2:12][C:13]#[CH:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:16][C:17]([NH2:19])=[S:18].O>C(O)C>[NH2:19][C:17]1[S:18][CH:2]=[C:3]([C:4](=[N:10][O:11][CH2:12][C:13]#[CH:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723790ThioureaHCID 53939675Ethyl 4-chloro-3-oxo-2-propargyloxyiminobutyrate

Product 1

HCID 53907014Ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetateYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 4-chloro-3-oxo-2-propargyloxyiminobutyrate (syn isomer, 61 g), thiourea (20 g), sodium acetate 3-hydrate (35.8 g), water (150 ml), and ethanol (180 ml) was stirred at 40° C. for 1.25 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 35.6 g).

Workup

  1. additionThe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record
ord-46fc5252a5cc4532a5ffd2671473a123
Source dataset
uspto-grants-1980_09
Patent number
US04220761

Reaction notes

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