Phenyl isocyanate → HCID 14650651, compound

HRID 982243Notes

Reaction equation

HRID 982243 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:19]1[O:20][CH2:21][CH:22]([OH:31])[CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1>ClCCCl>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:19]1[O:20][CH2:21][CH:22]([O:31][C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:24]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650594HCID 14650594, compound

Product 1

HCID 14650651HCID 14650651, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (2.3 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (4RS, 5RS)-2-(2-indolyl)-4-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (5.15 g) in 1,2-dichloroethane (50 cc). The solution obtained is stirred for 7 hours under reflux and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After two successive recrystallizations in diisopropyl ether, (4RS, 5RS)-2-(2-indolyl)-4-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (4 g), m.p. 166° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureunder reflux
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  4. customAfter two successive recrystallizations in diisopropyl ether

Sources & evidence

ORD record
ord-4dc2d04d18b84fd2afb3ceeb58f8155f
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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