O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 1,2-Diamino-4,5-difluoropyridinium 2,4,6-trimethylbenzenesulfonate

HRID 717561Notes

Reaction equation

HRID 717561 reaction equation
[NH2:1][O:2][S:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])(=[O:5])=[O:4].[F:15][C:16]1[C:21]([F:22])=[CH:20][N:19]=[C:18]([NH2:23])[CH:17]=1>ClCCl>[NH2:1][N+:19]1[CH:20]=[C:21]([F:22])[C:16]([F:15])=[CH:17][C:18]=1[NH2:23].[CH3:12][C:11]1[CH:10]=[C:9]([CH3:13])[CH:8]=[C:7]([CH3:14])[C:6]=1[S:3]([O-:5])(=[O:4])=[O:2]

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 717433744,5-Difluoropyridin-2-amine

Product 1

HCID 867296601,2-Diamino-4,5-difluoropyridinium 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(Aminooxy)sulfonyl]-1,3,5-trimethylbenzene was added to a solution of 4,5-difluoropyridin-2-amine (47-3; 0.1 g, 0.000769 mol) in dichloromethane (10 mL). The reaction mixture was stirred for 20 min. A precipitate formed and it was filtered and dried under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 8.91 (bs, 2H), 8.07-8.04 (m, 1H), 7.11-7.05 (m, 1H), 6.87 (s, 2H), 6.71 (s, 2H), 2.47 (s, 6H), 2.15 (s, 3H).

Workup

  1. customA precipitate formed
  2. filtrationit was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-872248ac0b904d0895ad03ce1673d729
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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