Reaction #918

Reaction equation

N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide

TFA

→

title compound

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

Solvents

methylene chloride

Conditions

Workup

1. 1
   ConcentrationThe orange reaction mixture was concentrated in vacuo
2. 2
   workup.ADDITIONThree portions of diethyl ether were added to the residue
3. 3
   Otherremoved by evaporation
4. 4
   Otherto remove residual TFA

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.

Source