Potassium Carbonate → HCID 15729165, compound

HRID 2380607Notes

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%).

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-e81876616ee944e1ba84e3904bc7f844
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369107

Reaction notes

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