Methanesulfonyl chloride → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide
Reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
Patent application WO0248132 describes a method for the synthesis of dronedarone using 2-n-butyl-5-nitro-benzofuran which is reduced, under pressure, with hydrogen in the presence of platinum oxide as catalyst in order to form 2-n-butyl-5-amino-benzofuran. This benzofuran derivative is then subjected to the action of methanesulfonyl chloride, which gives 2-n-butyl-5-methanesulfonamido-benzofuran which is treated with 4-[3-(di-n-butylamino)-propoxy]-benzoyl chloride to give dronedarone.
Sources & evidence
- ORD record
- ord-b74c403a19cd461993e79e84ddd11532
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871956B2
Reaction notes
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