Trifluoroacetic acid → N2,N2,1-Trimethyl-1H-pyrrole-2,3-disulfonamide

HRID 824

Reaction equation

HRID 824 reaction equation
CC([C:5]1[C:6]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:7]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[N:8]([CH3:10])[CH:9]=1)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:15][N:14]([CH3:16])[S:11]([C:7]1[N:8]([CH3:10])[CH:9]=[CH:5][C:6]=1[S:17]([NH2:20])(=[O:19])=[O:18])(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86749133(1,1-dimethylethyl)N2,N2,1-trimethyl-1H-pyrrole-2,3-disulfonamide

Product 1

HCID 53663278N2,N2,1-Trimethyl-1H-pyrrole-2,3-disulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.95 g (21 mmol) of N3 -(1,1-dimethylethyl)-N2,N2,1-trimethyl-1H-pyrrole-2,3-disulfonamide in 75 mL of methylene chloride under a nitrogen atmosphere 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 solid residue and removed by evaporation to remove residual TFA. The solids were suspended in diethyl ether and filtered to yield 4.52 g of the title compound as a solid, m.p. 146°-148° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThree portions of diethyl ether were added to the solid residue
  3. customremoved by evaporation
  4. customto remove residual TFA
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bce13e6e0f2b4556bf712059577ecdcd
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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