Trifluoroacetic acid → 2-(2-Chlorophenyl)ethene-1-sulfonamide

HRID 1272361Notes

Reaction equation

HRID 1272361 reaction equation
CC([NH:9][S:10](/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])(=[O:12])=[O:11])(C)CC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1/[CH:14]=[CH:13]/[S:10]([NH2:9])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609400(E)-2-(2-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

Product 1

HCID 110203382-(2-Chlorophenyl)ethene-1-sulfonamideYield 128.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-2-(2-Chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (4.55 g, 12.3 mmol) was stirred for 15 minutes in a 1:1 mixture of trifluoroacetic acid and dichloromethane (18 mL). The solution was concentrated in vacuo to afford a solid. The solid was washed with dichloromethane (5 mL) and heptane (150 mL) and was collected by suction filtration. The solid was dried under vacuum at room temperature to afford crude (E)-2-(2-chloro-phenyl)-ethenesulfonic acid amide (3.45 g) which was taken on to the next step without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto afford a solid
  3. washThe solid was washed with dichloromethane (5 mL) and heptane (150 mL)
  4. filtrationwas collected by suction filtration
  5. customThe solid was dried under vacuum at room temperature

Sources & evidence

ORD record
ord-c63ce6f3ba904d338c8e0b1fda7fd028
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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