Dimethylformamide dimethyl acetal → N'-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamide

HRID 83900

Reaction equation

HRID 83900 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>CC#N>[F:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:10])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4462753,5-Difluorobenzenesulfonamide

Product 1

HCID 66740661N'-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamideYield 45,829.801%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,5-difluorobenzenesulfonamide (154 g, 0.797 mol) in CH3CN (1 L) was added N,N-dimethylformamide dimethylacetal (224 mL, 1.67 mmol, 2.1 eq). After stirring 1 h, the reaction mixture was concentrated under reduced pressure. This material was triturated with Et2O and dried in vacuo to give N′-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamide (190 g, 96%) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.44-7.38 (m, 2H), 6.98-6.91 (m, 1H), 3.17 (s, 3H), 3.05 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThis material was triturated with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-68c1687ca38047928100c51d0c60a275
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Linked notes

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