Potassium Carbonate → HCID 15729165, compound

HRID 1656965Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of salt of potassium 2,4-difluorothiophenol (20 g), 2-acetamido-5-chlorothiazole (21 g) and potassium carbonate anhydrous (29.8 g) in N,N-dimethylformamide (400 ml) was stirred at 130° C. for 7 hours. The reaction mixture was concentrated under reduced pressure. The residue was triturated with water and 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, 70-230 mesh; Merck: 750 g) and eluted with a mixture of chloroform and methanol (50:1). The fractions containing the objective compound were combined and evaporated to dryness in vacuo to give 2-acetamido-5-(2,4-difluorophenylthio)thiazole (11.91 g, yield: 38.5%). mp: 156°-170° C. (dec.) IR (Nujol): 3160, 3060, 1695, 1585, 1560, 1295 cm-1

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was triturated with water
filtrationthe precipitates were collected by filtration
washwashed with water
customdried in vacuo
customto give solid
washeluted with a mixture of chloroform and methanol (50:1)
additionThe fractions containing the objective compound
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-9c166085dfdb4175b21960513ea39c16
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256675

Reaction notes

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