Phenyl isocyanate → HCID 14650699, compound

HRID 982254Notes

Reaction equation

HRID 982254 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:18]2[O:19][CH:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]([OH:24])[CH2:22][N:23]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]>ClCCCl>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[O:19][CH:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]([O:24][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:22][N:23]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650612HCID 14650612, compound

Product 1

HCID 14650699HCID 14650699, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (1.7 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-2-(3,4-dichlorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (4.7 g) in 1,2-dichloroethane (50 cc). The solution obtained is heated to reflux for 3 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 2 to 10 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-2-(3,4-dichlorophenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (4 g), m.p. 130° C., is obtained.

Workup

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

Sources & evidence

ORD record
ord-2de85592753c4fd9a5487d76f4e28377
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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