Benzenesulfonyl chloride → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-benzenesulfonamide

HRID 1797317Notes

Reaction equation

HRID 1797317 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:17].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[CH:5]=[CH:4][C:3]=1[C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 98191574-(2-Aminophenylamino)-2-chloro-2'-methylbenzophenone

Product 1

HCID 22174491N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (ice/water) solution of {2-chloro-4-[(2-aminophenyl)amino]phenyl}(2-methylphenyl)methanone (0.67 g, 2.0 mmol)(disclosed in WO 98/32730) in pyridine (10 mL) was added benzenesulfonyl chloride (0.32 mL, 2.5 mmol). The reaction mixture was warmed to room temperature. After stirring for 48 h, the reaction mixture was poured into ice water. The precipitate was filtered off, washed with water, and diethyl ether to afford the crude product. Crystallization from acetic acid afforded the title compound as a solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water, and diethyl ether
  3. customto afford the crude product
  4. customCrystallization from acetic acid

Sources & evidence

ORD record
ord-d089aa4a616f4d4d995f0323734e72eb
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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