4-(Trifluoromethyl)benzenesulfonyl chloride → N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]4-trifluoromethyl-benzenesulfonamide

HRID 1509906Notes

Reaction equation

HRID 1509906 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10].[F:17][C:18]([F:30])([F:29])[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:29])[F:30])=[CH:24][CH:23]=2)(=[O:27])=[O:26])=[C:3]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])[CH:4]=1

Participants

3

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 10214538(2-Amino-5-chlorophenyl)-pyridin-4-yl methanone

Product 1

HCID 10388551N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]4-trifluoromethyl-benzenesulfonamide

Procedure

The title compound was prepared according to the general procedure for the synthesis of N-Aryl-benzenesulfonamides previously described using 116 mg of (2-amino-5-chloro-phenyl)-pyridin-4-yl-methanone and 122 mg of 4-Trifluoromethyl-benzenesulfonyl chloride. 1H-NMR (400 MHz, CDCl3): δ 7.31 (d, 1H, J=2.8 Hz), 7.36 (m, 2H), 7.54-7.59 (m, 2H), 7.73 (d, 1H, J=8.0 Hz), 7.77 (d, 1H, J=9.2 Hz), 7.97 (d, 1H, J=8.0 Hz), 8.00 (s, 1H), 8.82 (dd, 2H, J=6.0 Hz, 1.2 Hz), 10.16 (s, 1H). MS: m/z 441.8 (M++1).

Sources & evidence

ORD record
ord-dd9bd648b66b47e399186660daa87405
Source dataset
uspto-grants-2012_07
Patent number
US08211896B2

Reaction notes

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