Sodium methanesulfinate → N-[5-(3,4-Bis-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

HRID 2247363Notes

Reaction equation

HRID 2247363 reaction equation
F[C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[Na+].[CH3:23][S:24]([O-:26])=[O:25].FC1C=C(C=CC=1S(C)(=O)=O)C=O>>[CH3:23][S:24]([C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9])(=[O:26])=[O:25]

Participants

4

Reactant 3

HCID 2733271Sodium methanesulfinateHCID 212517323-Fluoro-4-methanesulfonylbenzaldehydeHCID 57351276N-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 85861727N-[5-(3,4-Bis-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Procedure

This is isolated as a minor by product in the synthesis of N-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 64) when excess methane sulfinic acid sodium salt is added in the first step of the synthesis (64a). The resulting aldehyde is converted into the title compound by the procedure described in parts 64b-d.

Workup

  1. customThis is isolated as a minor by product

Sources & evidence

ORD record
ord-2d5360d03c6b40388a6e3a3edaafa340
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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