Phenyl isocyanate → HCID 67929863, compound

HRID 982275Notes

Reaction equation

HRID 982275 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:16]([OH:19])[CH2:17][N:18]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:2]([O:1][CH2:6][CH3:5])(=[O:34])[CH3:3].[CH:15]([O:14][CH:13]([CH3:10])[CH3:26])([CH3:16])[CH3:20].[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:16]([O:19][C:33](=[O:34])[NH:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:17][N:18]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67928881HCID 67928881, compound

Product 2

HCID 22281796Diisopropylether ethyl acetateHCID 67929863HCID 67929863, compoundYield 74%

Procedure

By working in a manner similar to that described in Example 38, but starting with (5RS, 6SR)-2-(4-morpholinophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.1 g) and phenyl isocyanate (0.46 g), and after purification of the crude product obtained by chromatography on silica (0.063-0.2 mm; 60 g) contained in a column 2.5 cm in diameter, eluting in 20-cc fractions with an ethyl acetate/methanol mixture (95:5 by volume), recovery and concentration under reduced pressure (2.7 kPa) of fractions 4 to 8 followed by recrystallization of the residue thereby obtained in an ethyl acetate/isopropyl ether mixture (50:50 by volume), (5RS, 6SR)-2-(4-morpholinophenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.55 g), m.p. 175° C., is obtained.

Workup

  1. customafter purification of the crude product
  2. customobtained by chromatography on silica (0.063-0.2 mm; 60 g)
  3. washeluting in 20-cc fractions with an ethyl acetate/methanol mixture (95:5 by volume), recovery and concentration under reduced pressure (2.7 kPa) of fractions 4 to 8
  4. customfollowed by recrystallization of the residue

Sources & evidence

ORD record
ord-b5e3c781469b405788de99e9a0c1b22b
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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