Ethanol → Ethyl 2-(2-aminothiazol-4-yl)-2-iso-butoxyiminoacetate

HRID 1462701Notes

Reaction equation

HRID 1462701 reaction equation
[CH2:1]([O:5][N:6]=[C:7]([C:13](=O)[CH2:14]Cl)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]([CH3:4])[CH3:3].[NH2:17][C:18]([NH2:20])=[S:19].C(O)C>O>[NH2:20][C:18]1[S:19][CH:14]=[C:13]([C:7](=[N:6][O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 54168146Ethyl 2-iso-butoxyimino-4-chloro-3-oxobutyrate

Product 1

HCID 53811669Ethyl 2-(2-aminothiazol-4-yl)-2-iso-butoxyiminoacetateYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-iso-butoxyimino-4-chloro-3-oxobutyrate (syn isomer, 31.9 g.), thiourea (9.72 g.), sodium acetate 3-hydrate (17.4 g.), ethanol (120 ml.) and water (80 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-iso-butoxyiminoacetate (syn isomer, 17.6 g.), mp 122° to 124° C.

Sources & evidence

ORD record
ord-652e39d2d3e340bf86cbc9482dbc7d94
Source dataset
uspto-grants-1984_07
Patent number
US04460583

Reaction notes

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