Sodium hydride → N-[4-(Benzothiazol-2-ylmethylthio)phenyl]acetamide
Reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].Br[CH2:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1>CN(C)C=O.C(OCC)(=O)C>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[CH2:15][S:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[CH:8][CH:9]=1Participants
Procedure
79.7 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 303.1 mg of 4-acetamidothiophenol in 6 ml of dimethylformamide at room temperature, followed by the addition of a solution of 454.8 mg of 2-bromomethyl-benzothiazole in 1 ml of dimethylformamide. The resulting mixture was stirred at room temperature for 2 hours, after which the reaction mixture was diluted with ethyl acetate, washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 462.7 mg (yield 81%) of the title compound as a solid having a melting point of 147° to 149° C.
Workup
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was then removed by evaporation under reduced pressure
- customthe resulting residue was purified by column chromatography through silica gel using a 1:2
- additionby volume mixture of hexane and ethyl acetate as the eluent
Sources & evidence
- ORD record
- ord-e43ff76f29be45ffb85686949e392401
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05736487
Reaction notes
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