Ethanol → Ethyl 2-(2-aminothiazol-4-yl)2-n-hexyloxyiminoacetate

HRID 1284699Notes

Reaction equation

HRID 1284699 reaction equation
[CH2:1]([O:7][N:8]=[C:9]([C:15](=O)[CH2:16]Cl)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:19][C:20]([NH2:22])=[S:21].C(O)C>O>[NH2:22][C:20]1[S:21][CH:16]=[C:15]([C:9](=[N:8][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 54042766Ethyl 4-chloro-2-[(hexyloxy)imino]-3-oxobutanoate

Product 1

HCID 53940552Ethyl 2-(2-aminothiazol-4-yl)2-n-hexyloxyiminoacetateYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-n-hexyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 55.6 g.), thiourea (15.2 g.), sodium acetate 3-hydrate (27.2 g.), ethanol (280 ml.) and water (140 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-n-hexyloxyiminoacetate (syn isomer, 29.3 g.), mp 77° to 78° C.

Sources & evidence

ORD record
ord-9ff42d655cbd49d9b4633d2e13c71076
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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