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

HRID 1284690Notes

Reaction equation

HRID 1284690 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:19][C:20]([NH2:22])=[S:21].O>C(O)C>[NH2:22][C:20]1[S:21][CH:2]=[C:3]([C:4](=[N:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723790ThioureaHCID 53775948Ethyl 4-chloro-2-[(cyclohexyloxy)imino]-3-oxobutanoate

Product 1

HCID 53692631Ethyl 2-(2-aminothiazol-4-yl)-2-cyclohexyloxyiminoacetateYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-chloro-2-cyclohexyloxyimino-3-oxobutyrate (syn isomer, 27.8 g.), thiourea (7.7 g.), sodium acetate 3-hydrate (13.7 g.), water (70 ml.) and ethanol (140 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-cyclohexyloxyiminoacetate (syn isomer, 3.6 g.), mp. 125° to 126° C.

Sources & evidence

ORD record
ord-34972a56fa1646c9be2a537884ed2b5b
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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