Triethylamine → (E)-4-Chloro-2-(2-(3,4-dichlorophenyl)vinylsulfonamido)benzenesulfonamide

HRID 2283375Notes

Reaction equation

HRID 2283375 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[Cl:13][C:14]1[CH:15]=[C:16](/[CH:21]=[CH:22]/[S:23](Cl)(=[O:25])=[O:24])[CH:17]=[CH:18][C:19]=1[Cl:20].C(N(CC)CC)C>ClCCl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:2]([NH:1][S:23](/[CH:22]=[CH:21]/[C:16]2[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=2)(=[O:25])=[O:24])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 777902-Amino-4-chlorobenzenesulphonamideHCID 22719686(E)-2-(3,4-dichlorophenyl)ethenesulfonyl chloride

Product 1

HCID 57750903(E)-4-Chloro-2-(2-(3,4-dichlorophenyl)vinylsulfonamido)benzenesulfonamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-chlorobenzenesulfonamide (100 mg, 0.48 mmol) and (E)-2-(3,4-dichlorophenyl)ethenesulfonyl chloride (171 mg, 0.63 mmol) were dissolved in anhydrous dichloromethane (5 mL) and were flushed with argon. Anhydrous triethylamine (0.155 mL, 1.11 mmol) was added and the reaction was stirred at room temperature under an inert atmosphere over night. The reaction was quenched using 2 M hydrochloric acid (20 mL) and extracted with dichloromethane. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated under vacuum to give 194 mg (91% yield) of the title compound.

Workup

  1. customwere flushed with argon
  2. customThe reaction was quenched
  3. extractionextracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bd24960907dd4c8485d631ba43c33bd7
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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