p-Toluenesulfonyl isocyanate → HCID 178498476, compound

HRID 1195655Notes

Reaction equation

HRID 1195655 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([N:25]=C=O)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(#N)C>[C:16]1([CH3:28])[CH:17]=[CH:18][C:19]([S:22]([N:25]=[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3]2)(=[O:23])=[O:24])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 178498498HCID 178498498, compound

Product 1

HCID 178498476HCID 178498476, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to the procedure of Wright, Synthesis, 1984, 1058, methyl 4-hydroxy-2-quinolinecarboxylate (2.03 g, 0.01 m) and p-toluenesulfonyl isocyanate (1.97 g, 0.01 m) were mixed in reagent grade acetonitrile at RT. The heterogeneous mixture was heated at reflux until the evolution of COz had ceased (ca 2-3 hours). During this time a yellow solid formed. After cooling to RT, the yellow solid was collected by filtration, washed with acetonitrile, and dried to give methyl 4-(p-toluenesulfonylimino)-1,4-dihydroquinoline-2-carboxylate (2.93 g, 82%), melting point of 264°-265° C. (dec.), as a yellow solid.

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureat reflux until the evolution of COz
  3. custom(ca 2-3 hours)
  4. customDuring this time a yellow solid formed
  5. filtrationthe yellow solid was collected by filtration
  6. washwashed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-f9de088f5f19412aa86e720f83208c9b
Source dataset
uspto-grants-1992_05
Patent number
US05112821

Reaction notes

Loading…