2-Amino-4,6-dimethyl-3-pyridinecarbonitrile → N-[(3-Cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide

HRID 4130Notes

Reaction equation

HRID 4130 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([CH3:11])[N:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])([O-:14])=[O:13]>C(#N)C>[C:8]([C:7]1[C:2]([NH:1][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])(=[O:22])=[O:23])=[O:26])=[N:3][C:4]([CH3:11])=[CH:5][C:6]=1[CH3:10])#[N:9]

Participants

4

Reactant 2

HCID 2304712-Amino-4,6-dimethyl-3-pyridinecarbonitrileHCID 111388842-Nitrobenzenesulfonyl isocyanate

Product 1

HCID 14050202N-[(3-Cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 0.5 g (4.3 mmol) 2-amino-4,6-dimethyl-3-pyridinecarbonitrile [Archiv. Pharm., 288, 174 (1955)] in 20 ml of acetonitrile was added 1.3 g (5.7 mmol) o-nitrobenzenesulfonyl isocyanate. The mixture was then heated to reflux (80°) for four hours followed by stirring at ambient temperature overnight. A crystalline product was collected, 0.5 g, m.p. 174°-176° dec. An infrared spectrum (nujol mull) exhibited absorptions at 1700, 1720 and 2240 cm-1 ; and a proton magnetic resonance spectrum (90 MHz NMR) exhibited absorptions at 2.5 (s, 3H), 2.6 (s, 3H), 7.05 (s, H), 7.7 (s br, NH), 7.8 (m, 3H), 8.4 (m, 1H), 9.7 (s br, NH) ppm indicating the title compound.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux (80°) for four hours
  3. customA crystalline product was collected

Sources & evidence

ORD record
ord-a4c6ac19a65248798aac4e008fbbaf15
Source dataset
uspto-grants-1988_02
Patent number
US04723991

Reaction notes

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