Trifluoroacetic acid → (1E)-2-(4-Chlorophenyl)ethenesulfonamide

HRID 1272355Notes

Reaction equation

HRID 1272355 reaction equation
CC([NH:9][S:10](/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=[O:12])=[O:11])(C)CC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15](/[CH:14]=[CH:13]/[S:10]([NH2:9])(=[O:11])=[O:12])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17748075(E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

Product 1

HCID 6212331(1E)-2-(4-Chlorophenyl)ethenesulfonamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.0 g, 15.2 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (10 ml) and the mixture was stirred for 15 min. The mixture was concentrated in vacuo to afford a solid. The solid was washed with dichloromethane (5 ml) and heptane (150 ml). The resultant solid was collected by suction filtration. The solid was dried under vacuum at room temperature to afford (E)-2-(4-chloro-phenyl)-ethenesulfonic acid amide (2.95 g, 89%).

Workup

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

Sources & evidence

ORD record
ord-f0e02833935c49e3bb4fd045b332985c
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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