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

HRID 1092981Notes

Reaction equation

HRID 1092981 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-e7cee021a9564acb810c143eb8c7f07b
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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