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

HRID 2259189Notes

Reaction equation

HRID 2259189 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. 1H NMR(Me2SO-d6, 200 MHz.) δ: 6.99(bs,2H), 6.88(d,1H), 6.34(d,1H), 3.47(s,3H), 2.96(s,3H), 2.81(s,3H).

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-c7fb2f6b0ce54c51964100c3d03d00cd
Source dataset
uspto-grants-1995_12
Patent number
US05472933

Reaction notes

Loading…