Thionyl Chloride → N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}-2-(trifluoromethyl)benzenesulfonamide

HRID 2401029Notes

Reaction equation

HRID 2401029 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=2)=[N:17][CH:16]=[CH:15][N:14]=1)(=[O:11])=[O:10].S(Cl)([Cl:31])=O>>[Cl:31][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:13]([NH:12][S:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:28])([F:27])[F:1])(=[O:11])=[O:10])=[N:14][CH:15]=[CH:16][N:17]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 575860712-trifluoromethyl-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide

Product 1

HCID 57444250N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}-2-(trifluoromethyl)benzenesulfonamideYield 96%

Procedure

Following the general method as outlined for Intermediate 8, starting from 2-trifluoromethyl-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide and thionyl chloride, the title compound was isolated, after evaporation and recrystallization, as a white solid in 96% yield (97% purity by HPLC).

Sources & evidence

ORD record
ord-6fa944b9339a460593df8922a28d9e07
Source dataset
uspto-grants-2014_08
Patent number
US08796280B2

Reaction notes

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