Trifluoroacetic acid → N-benzylaminosulfonamide

HRID 1735938Notes

Reaction equation

HRID 1735938 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].F[C:7](F)(F)C(O)=O.[C:13]1(OC)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:7]([NH:4][S:1]([NH2:5])(=[O:3])=[O:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 82267Sulfamide

Product 1

HCID 12354987N-benzylaminosulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The condensed sulfamide having a t-butoxycarbonyl protecting group obtained as Sample No. 1 of Example 1 is dissolved in a mixture of dichloromethane (15 vol.) and anisole (15 vol.) under ice cooling, and trifluoroacetic acid (15 vol.) is added thereto. The mixture is stirred for 50 minutes, and for 1 hour after the ice bath is removed. The reaction mixture is concentrated. The residue is recrystallized from a mixture of ether and petroleum ether (1:6) to give benzylsulfamide. Colorless crystals. Yield: 90%.

Workup

  1. customobtained as Sample No
  2. customfor 1 hour after the ice bath is removed
  3. concentrationThe reaction mixture is concentrated
  4. customThe residue is recrystallized from a mixture of ether and petroleum ether (1:6)

Sources & evidence

ORD record
ord-40f5c0f92d9a4e858dab77033cb15f6b
Source dataset
uspto-grants-1996_07
Patent number
US05539102

Reaction notes

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