4-(3-Chloro-2-cyanophenoxy)benzenesulfonyl chloride → 4-(3-chloro-2-cyano-phenoxy)-N-[3-(2-dimethylamino-ethoxy)-4-trifluoromethyl-phenyl]-benzenesulfonamide

HRID 22765

Reaction equation

HRID 22765 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:16])[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].[Cl:18][C:19]1[C:20]([C:36]#[N:37])=[C:21]([CH:33]=[CH:34][CH:35]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[Cl:18][C:19]1[C:20]([C:36]#[N:37])=[C:21]([CH:33]=[CH:34][CH:35]=1)[O:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:16][C:8]2[CH:9]=[CH:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:17])[CH3:1])[CH:7]=2)(=[O:30])=[O:31])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 27769174-(3-Chloro-2-cyanophenoxy)benzenesulfonyl chlorideHCID 17756283Benzenamine, 3-[2-(dimethylamino)ethoxy]-4-(trifluoromethyl)-

Product 1

HCID 101657614-(3-chloro-2-cyano-phenoxy)-N-[3-(2-dimethylamino-ethoxy)-4-trifluoromethyl-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3-(2-dimethylamino-ethoxy)-4-trifluoromethyl-phenylamine (0.10 g, 0.4 mmol) in CHCl3 (2.5 mL) was added 4-(3-chloro-2-cyano-phenoxy) benzenesulfonyl chloride (0.13 g, 0.4 mmol) at rt. After stirring at rt for 72 h, the solvent was evaporated and the residue was purified by vacuum filtration through silica gel eluting successively with 4% MeOH in CH2Cl2 and 10% MeOH in CH2Cl2 followed by a mixture of CH2Cl2, MeOH and conc. NH4OH (90:10:1). The solvent was removed from the desired fractions and the residue was recrystallized from a mixture of MeOH and EtOAc to afford the title compound as a white solid; yield 0.01 g (5%): LCMS 540 (M++H).

Workup

  1. customthe solvent was evaporated
  2. filtrationthe residue was purified by vacuum filtration through silica gel eluting successively with 4% MeOH in CH2Cl2 and 10% MeOH in CH2Cl2
  3. additionfollowed by a mixture of CH2Cl2, MeOH and conc. NH4OH (90:10:1)
  4. customThe solvent was removed from the desired fractions
  5. customthe residue was recrystallized from a mixture of MeOH and EtOAc

Sources & evidence

ORD record
ord-f654829ee46b47468eb0b6f8ed977fb2
Source dataset
uspto-grants-2005_02
Patent number
US06849635B2

Linked notes

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