2-Amino-5-chlorobenzenesulphonamide → (E)-5-chloro-2-(2-(4-chloro-2-methoxyphenyl)vinylsulfonamido)benzenesulfonamide

HRID 2283335Notes

Reaction equation

HRID 2283335 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[S:22](Cl)(=[O:24])=[O:23])=[C:16]([O:26][CH3:27])[CH:15]=1>N1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:22](/[CH:21]=[CH:20]/[C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][C:16]=2[O:26][CH3:27])(=[O:23])=[O:24])=[C:3]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 122955502-Amino-5-chlorobenzenesulphonamideHCID 22711054(E)-2-(4-chloro-2-methoxyphenyl)ethenesulfonyl chloride

Product 1

HCID 57751036(E)-5-chloro-2-(2-(4-chloro-2-methoxyphenyl)vinylsulfonamido)benzenesulfonamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-5-chlorobenzenesulfonamide (0.041 g, 0.20 mmol) and (E)-2-(4-chloro-2-methoxyphenyl)ethenesulfonyl chloride (0.053 g, 0.20 mmol) in pyridine (2 mL) was stirred at room temperature over night. The reaction mixture was concentrated, 1 M hydrochloric acid was added and the mixture was extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was evaporated to give 0.087 g (99% yield) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1 M hydrochloric acid was added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-da650443174d438fba1de736f5cb837b
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

Loading…