Water → N-[5-(4-Fluoro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

HRID 2247338Notes

Reaction equation

Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=1)[C:3](=O)[CH3:4].[C:17]([NH:20][C:21]([NH2:23])=[S:22])(=[O:19])[CH3:18].O.C(OCC)(=O)C>C(O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[S:22][C:21]([NH:20][C:17](=[O:19])[CH3:18])=[N:23][C:3]=2[CH3:4])=[CH:7][C:8]=1[S:13]([CH3:16])(=[O:15])=[O:14]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-bromo-1-(4-fluoro-3-methanesulfonyl-phenyl)-propan-2-one (Example 47c) (0.17 g, 0.55 mmol) and N-acetylthiourea (0.065 g, 0.55 mmol) in ethanol is heated at 70° C. for 3 hours then at room temperature over two days. The reaction mixture is poured into water (200 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford a viscous solid. This solid in a minimum amount of ethyl acetate is sonicated to give a suspension which is then heated until all solid has dissolved then left to cool to room temperature overnight. The white crystalline solid is filtered off to afford the titled compound.

Workup

extractionextracted with ethyl acetate (3×50 ml)
dry with materialThe combined organic layers are dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto afford a viscous solid
customto give a suspension which
temperatureis then heated until all solid
dissolutionhas dissolved
waitthen left
temperatureto cool to room temperature overnight
filtrationThe white crystalline solid is filtered off

Sources & evidence

ORD record: ord-1fc0031df56645d3b1b04ebef8f49c84
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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