Trifluoroacetic acid → 2-(Thiophen-2-yl)ethene-1-sulfonamide

HRID 1272080Notes

Reaction equation

HRID 1272080 reaction equation
CC([NH:9][S:10](/[CH:13]=[CH:14]/[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:12])=[O:11])(C)CC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[S:16]1[CH:17]=[CH:18][CH:19]=[C:15]1/[CH:14]=[CH:13]/[S:10]([NH2:9])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609959(E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

Product 1

HCID 149124362-(Thiophen-2-yl)ethene-1-sulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-2-Thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.17 g, 17.2 mmol) was stirred for 15 minutes in a 1:1 mixture of trifluoroacetic acid and dichloromethane (40 mL). The mixture was concentrated in vacuo to afford a solid that was washed with dichloromethane (10 mL) in heptane (100 mL). The resultant solid was collected by suction filtration and dried under vacuum at ambient temperature to afford (E)-2-thiophen-2-yl-ethenesulfonic acid amide (2.89 g, 89%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford a solid
  3. washthat was washed with dichloromethane (10 mL) in heptane (100 mL)
  4. filtrationThe resultant solid was collected by suction filtration
  5. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-9bd2d0fefc85440e8a56200460a461ff
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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