Phenyl isocyanate → HCID 67928888, compound

HRID 982279Notes

Reaction equation

HRID 982279 reaction equation
[C:1]1([CH:7]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)=[N:10][CH2:9][CH:8]2[OH:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCCl>[C:1]1([CH:7]2[O:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:17][CH:18]=3)=[N:10][CH2:9][CH:8]2[O:24][C:32](=[O:33])[NH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67928877HCID 67928877, compound

Product 1

HCID 67928888HCID 67928888, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (5RS, 6RS)-6-phenyl-2-[4-(trifluoromethoxy)phenyl]-5,6-dihydro-4H-1,3-oxazin-5-ol (6 g) and phenyl isocyanate (2.4 g) in 1,2-dichloroethane (100 cc) is heated to a temperature in the region of 60° C. for 5 hours. After being cooled, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue obtained is purified by chromatography on silica (0.063-0.2 mm; 200 g) contained in a column 3.5 cm in diameter, eluting in 20-cc fractions with an ethyl acetate/cyclohexane mixture (30:70 by volume). Fractions 4 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in diisopropyl ether (5 cc). (5RS, 6SR)-6-Phenyl-5-phenylcarbamoyloxy-2-[4-(trifluoromethoxy)phenyl]-5,6-dihydro-4H-1,3-oxazine (1.1 g), m.p. 128° C., is thereby obtained.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customthe residue obtained
  4. customis purified by chromatography on silica (0.063-0.2 mm; 200 g)
  5. washeluting in 20-cc fractions with an ethyl acetate/cyclohexane mixture (30:70 by volume)
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized in diisopropyl ether (5 cc)

Sources & evidence

ORD record
ord-95067acac742410a9d2d551d5010df61
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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