Phenyl isocyanate → HCID 14650705, compound

HRID 982260Notes

Reaction equation

HRID 982260 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:7][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]([OH:12])[CH2:10][N:11]=2)=[CH:2]1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:7][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]([O:12][C:26](=[O:27])[NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][N:11]=2)=[CH:2]1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650618HCID 14650618, compound

Product 1

HCID 14650705HCID 14650705, compoundYield 40%

Procedure

Working in a manner similar to that described in Example 12, but starting with (5RS, 6SR)-2-(3-furyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (2.6 g) and phenyl isocyanate (3.8 g), and after purification of the solid obtained by chromatography on a column (height: 30 cm; diameter: 4 cm) of silica (0.2-0.063 mm), eluting with a mixture of dichloroethane and ethyl acetate (90:10 by volume) and collecting 40-cc fractions, fractions 20 to 28 being combined and concentrated to dryness under reduced pressure (4 kPa) at 45° C., followed by recrystallizaiton in isopropyl ether (10 cc), (5RS, 6SR)-2-(3-furyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (1.55 g), m.p. 130° C., is obtained.

Workup

  1. customafter purification of the solid
  2. customobtained by chromatography on a column (height: 30 cm; diameter: 4 cm) of silica (0.2-0.063 mm)
  3. washeluting with a mixture of dichloroethane and ethyl acetate (90:10 by volume)
  4. customcollecting 40-cc fractions, fractions 20 to 28 being
  5. concentrationconcentrated to dryness under reduced pressure (4 kPa) at 45° C.

Sources & evidence

ORD record
ord-6ff8e8dbb5f54e52b72b31ce4038f4ec
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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