p-Toluenesulfonyl isocyanate → HCID 19093722, compound

HRID 2254898Notes

Reaction equation

HRID 2254898 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14]([C:22]1C(=O)[CH:26]=[C:25]([CH2:29][CH3:30])[NH:24][C:23]=1[CH3:31])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[C:14]([C:22]1[C:23]([CH3:31])=[N:24][C:25]([CH2:29][CH3:30])=[CH:26][C:12]=1[NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 14950493HCID 14950493, compound

Product 1

HCID 19093722HCID 19093722, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methylphenylsulphonyl isocyanate (0.66 ml) was added to a stirred suspension of compound C (0.48 g) in acetonitrile and the mixture was heated at reflux for 2.5 hours. The mixture was cooled to ambient temperature and the product was collected by filtration to give 3-benzoyl-6-ethyl-2-methyl-4-[(4-methylphenylsulphonyl)amino]pyridine (D) (0.65 g) as a solid, m.p. 244°-246° C.; NMR (d6 -DMSO): 1.19(t, 3H), 2.13(s, 3H), 2.31(s, 3H), 2.65(q, 2H), 7.08(s, 1H), 7.15(d, 2H), 7.32(d, 2H), 7.50-7.68(m, 5H), 12.63(s, 1H); mass spectrum (+ve FAB, glycerol/methanol): 395(M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-302a76a9ea094f309b5c96a1cf7e0843
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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