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

HRID 1388473Notes

Reaction equation

HRID 1388473 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+]>O.C(O)C>[CH2:1]([O:6][N:7]=[C:8]([C:14]1[N:18]=[C:19]([NH2:21])[S:20][CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 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 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-pentyloxyimino-3-oxo-4-chlorobutyrate (syn isomer) (51.1 g.) and thiourea (14.7 g.) were reacted in the presence of sodium acetate trihydrate (26.4 g.) in a mixture of water (125 ml.) and ethanol (175 ml.) according to a similar manner to that of Preparation 8-(10) to give crystals of ethyl 2-pentyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (28.7 g.), mp 86° to 88° C.

Workup

  1. customof Preparation 8-(10)

Sources & evidence

ORD record
ord-927ce10fec9f4155bbd7783eaf404ddf
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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