Trifluoroacetic acid → 3-(Aminosulfonyl)-N,N,1-trimethyl-1H-pyrrole-2-carboxamide

HRID 826

Reaction equation

HRID 826 reaction equation
CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])(=[O:8])=[O:7])(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 196938293-[[(1,1-dimethylethyl)amino]sulfonyl]N,N,1-trimethyl-1H-pyrrole-2-carboxamide

Product 1

HCID 196938183-(Aminosulfonyl)-N,N,1-trimethyl-1H-pyrrole-2-carboxamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.63 g of 3-[[(1,1-dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide in 75 mL of methylene chloride was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 4.21 g of the title compound as a gray solid, m.p. 185°-190.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThree portions of diethyl ether were added to the residue
  3. customremoved by evaporation
  4. customto remove residual TFA

Sources & evidence

ORD record
ord-4d0fbf7c4db24ef2820d2d87a9754e6c
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

Loading…