Phenyl isocyanate → HCID 14650667, compound

HRID 982264Notes

Reaction equation

[CH3:1][CH:2]1[CH:7]([OH:8])[CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:3]1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:15]1([C:4]2[O:5][CH:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]([O:8][C:28](=[O:29])[NH:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:2]([CH3:1])[N:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 14650628HCID 14650628, compound

Product 1

HCID 14650667HCID 14650667, compoundYield 15%

Procedure

Working in a manner similar to that described in Example 12, but starting with 4-methyl-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (mixture of 4SR, 5RS, 6SR and 4RS, 5RS, 6SR diastereoisomers, 50:50 mole/mole; 3.7 g) and phenyl isocyanate (5 g), then purifying the oil obtained by chromatography on a column (height: 45 cm; diameter: 4 cm) of silica, eluting with a mixture of cyclohexane and ethyl acetate (85:15 by volume) and collecting 25-cc fractions, fractions 22 to 25 being combined and concentrated to dryness under reduced pressure (4 kPa) at 45° C., followed by recrystallization of the solid obtained in acetonitrile, (4SR, 5RS, 6SR)-2,6-diphenyl-4-methyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.8 g), m.p. 150° C., is obtained.

Workup

custompurifying the oil
customobtained by chromatography on a column (height: 45 cm; diameter: 4 cm) of silica
washeluting with a mixture of cyclohexane and ethyl acetate (85:15 by volume)
customcollecting 25-cc fractions, fractions 22 to 25 being
concentrationconcentrated to dryness under reduced pressure (4 kPa) at 45° C.
customfollowed by recrystallization of the solid
customobtained in acetonitrile

Sources & evidence

ORD record: ord-8dfd0202990946c093fec28ca2b03658
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994569

Reaction notes

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