Ethyl Acetate → HCID 59296133, compound

Reaction equation

[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18](=[O:25])[CH2:19][C:20](=O)[CH:21](Br)[CH3:22].[CH2:26](OC(=O)C)C>CC(C)=O>[CH2:16]([O:17][C:18](=[O:25])[CH2:19][C:20]1[N:9]=[C:7]([C:6]2[CH:5]=[CH:4][C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])=[CH:11][CH:10]=2)[S:8][C:21]=1[CH3:22])[CH3:26]

Participants

Procedure

0 g 4-Pentafluorosulfanyl-thiobenzamide and 9.93 g 4-bromo-3-oxo-pentanoic acid methyl ester were dissolved in 30 ml acetone and refluxed for one hour. The cooled reaction mixture was diluted by adding 250 ml ethylacetate and washed three times with saturated NaHCO3 solution. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography with the eluent n-heptane:ethyl acetate=5:1 to provide 4.5 g [5-Methyl-2-(4-pentafluorosulfanyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester as an oil which solidified upon standing.