Water → Ethyl 2-(2-aminothiazol-4-yl)-2-(2-benzoyloxyethoxyimino)acetate

HRID 745374Notes

Reaction equation

HRID 745374 reaction equation
[C:1]([O:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20](=O)[CH2:21]Cl)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]([NH2:27])=[S:26].C([O-])(=O)C.[Na+].O>C(O)C>[NH2:27][C:25]1[S:26][CH:21]=[C:20]([C:14](=[N:13][O:12][CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 53906646Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate

Product 1

HCID 53954764Ethyl 2-(2-aminothiazol-4-yl)-2-(2-benzoyloxyethoxyimino)acetateYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate (syn isomer, 20 g.), thiourea (7.76 g.), sodium acetate (8.37 g.), water (75 ml.) and ethanol (75 ml.) were treated in a similar manner to that of Example A-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-benzoyloxyethoxyimino)acetate (syn isomer, 9 g.).

Sources & evidence

ORD record
ord-80ad761531f74804b3c2dc823b23ad46
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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