Trifluoroacetic acid → 2-Bromo-1-methyl-1H-pyrrole-3-sulfonamide

HRID 2259183

Reaction equation

HRID 2259183 reaction equation
[Br:1][C:2]1[N:3]([CH3:15])[CH:4]=[CH:5][C:6]=1[S:7]([NH:10]C(C)(C)C)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[N:3]([CH3:15])[CH:4]=[CH:5][C:6]=1[S:7]([NH2:10])(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 196938302-bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

Product 1

HCID 196938442-Bromo-1-methyl-1H-pyrrole-3-sulfonamideYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.11 g (24 mmol) of 2-bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 50 mL methylene chloride under a nitrogen atmosphere was added 50 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 crude residue and was removed by evaporation to remove residual TFA, which yielded 1.23 g of the title compound as a light brown solid. 1H NMR (Acetone-d6, 200 MHz.) δ: 7.36(d,1H), 6.49(d,1H), 6.3(bs,2H) 3.68(s,3H).

Workup

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

Sources & evidence

ORD record
ord-24fca5966e304194948bc21b192c7f7a
Source dataset
uspto-grants-1995_12
Patent number
US05472933

Linked notes

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