Potassium Carbonate → N-(5-((4-(Hydroxy(oxido)amino)phenyl)thio)-1,3-thiazol-2-yl)acetamide

HRID 1656945Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:20][C:17]2[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-acetylamino-5-chlorothiazole (5 g), 4-nitrothiophenol (4.83 g) and potassium carbonate (7.8 g) in N,N-dimethylformamide (100 ml) was heated at 120° C. for 3 hours with stirring. The reaction mixture was poured into ice-water. The precipitates were collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 200 g) and eluted with a mixture of n-hexane and ethyl acetate (3:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-acetylamino-5-(4-nitrophenylthio)thiazole (3.74 g, yield: 50.2%). mp: 250°-255° C. (dec.)

Workup

filtrationThe precipitates were collected by filtration
washwashed with water
customdried in vacuo
customto give solid
washeluted with a mixture of n-hexane and ethyl acetate (3:1)
additionThe fractions containing the objective compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ca86032daf094d79b09ec7f61ad04efa
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256675

Reaction notes

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