Sodium Bicarbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetate

HRID 894747Notes

Reaction equation

HRID 894747 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:16](=O)[CH2:17]Cl)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]([NH2:23])=[S:22].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O.C(O)C>[NH2:23][C:21]1[S:22][CH:17]=[C:16]([C:10](=[N:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:20]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 53794160Ethyl 2-benzyloxyimino-4-chloro-3-oxobutyrate

Product 1

HCID 54194304Ethyl 2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetateYield 71.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-benzyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 51.4 g.), thiourea (17.5 g.) and sodium acetate (31.3 g.) in a mixture of water (130 ml.) and ethanol (130 ml.) was stirred at 40° to 45° C. for 2.5 hours. The resultant solution was adjusted to pH 6.5 with aqueous sodium bicarbonate and the precipitates were collected by filtration and washed with diisopropyl ether to give ethyl 2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetate (syn isomer, 39.78 g.).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-87190cedb2224dc8a155456405ff7d36
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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