Trifluoroacetic acid → 2-[(Methoxyimino)methyl]-1-methyl-1H-pyrrole-3-sulfonamide

HRID 822

Reaction equation

HRID 822 reaction equation
CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][C:10]=1[CH:14]=[N:15][O:16][CH3:17])(=[O:8])=[O:7])(C)C.[C:18](O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][O:16][N:15]=[CH:14][C:10]1[N:11]([CH3:18])[CH:12]=[CH:13][C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136144806N-(1,1-Dimethylethyl)-2-[(methoxyimino)methyl]-1H-pyrrole-3-sulfonamide

Product 1

HCID 541233872-[(Methoxyimino)methyl]-1-methyl-1H-pyrrole-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.74 g (21.9 mmol) of N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide in 75 mL methylene chloride under a nitrogen atmosphere was add 75 mL of TFA. The clear orange reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The orange 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 3.49 g of the title compound as a gray solid, m.p. 120°-122° C.

Workup

  1. concentrationThe orange 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-0d13730de7524a88a677102766469c81
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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