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

HRID 1081243Notes

Reaction equation

HRID 1081243 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-252c72d7c0894a549c76e99ca5c6cfeb
Source dataset
uspto-grants-1996_12
Patent number
US05585328

Reaction notes

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