Ethanol → Ethyl 2-(2-aminothiazol-4-yl)-2-pentyloxyiminoacetate

HRID 1650453Notes

Reaction equation

HRID 1650453 reaction equation
[CH2:1]([O:6][N:7]=[C:8]([C:14](=O)[CH2:15]Cl)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:18][C:19]([NH2:21])=[S:20].O.O.O.C([O-])(=O)C.[Na+].C(O)C>O>[NH2:21][C:19]1[S:20][CH:15]=[C:14]([C:8](=[N:7][O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723790ThioureaHCID 23665404Sodium Acetate TrihydrateHCID 53992771Ethyl 4-chloro-3-oxo-2-[(pentyloxy)imino]butanoate

Product 1

HCID 54426052Ethyl 2-(2-aminothiazol-4-yl)-2-pentyloxyiminoacetateYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-pentyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 51.1 g.), thiourea (14.7 g.), sodium acetate trihydrate (26.4 g.), ethanol (175 ml.) and water (125 ml.) were treated in a similar manner to that of Example F -(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-pentyloxyiminoacetate (syn isomer, 28.7 g.), mp 86° to 88° C.

Sources & evidence

ORD record
ord-c10253e8dbd34723a451e8509edad810
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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