Phenyl isocyanate → HCID 67928886, compound

HRID 982285Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Phenyl isocyanate (0.7 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-2-(2-naphthyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.8 g) in 1,2-dichloroethane (21 cc). The solution obtained is heated to 80° C. for 4 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is purified by chromatography on silica (0.063-0.2 mm; 200 g) contained in a column 2.5 cm in diameter, collecting 20-cc fractions. The fractions 12 to 20, eluted with dichloromethane, are concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in acetonitrile, (5RS, 6SR)-2-(2-naphthyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.9 g), m.p. 163° C., is obtained.

Workup

customThe solution obtained
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe solid obtained
customis purified by chromatography on silica (0.063-0.2 mm; 200 g)
customcollecting 20-cc fractions
washThe fractions 12 to 20, eluted with dichloromethane
concentrationare concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
customAfter recrystallization in acetonitrile

Sources & evidence

ORD record: ord-a295396b917a4ad783107cb757e898f0
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994569

Reaction notes

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