Phenyl isocyanate → HCID 14650695, compound

HRID 982252Notes

Reaction equation

HRID 982252 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[O:18][CH:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]([OH:23])[CH2:21][N:22]=2)[CH:14]=[CH:15][CH:16]=1>ClCCCl>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[O:18][CH:19]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:20]([O:23][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:21][N:22]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650608HCID 14650608, compound

Product 1

HCID 14650695HCID 14650695, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (1.43 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-2-(3-chlorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (3.55 g) in 1,2-dichloroethane (45 cc). The solution is heated to reflux for 4 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by chromatography on silica (0.063-0.2 mm; 100 g) contained in a column 2.5 cm in diameter [eluent: cyclohexane/ethyl acetate (7:3 by volume)], collecting 20-cc fractions. Fractions 6 to 11 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-2-(3-chlorophenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (2.4 g), m.p. 126° C., is obtained.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 100 g)
  5. customcollecting 20-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-48c11b2ae1ca4066b7c6290905c96d1f
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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