Phenyl isocyanate → HCID 14650711, compound

HRID 982268Notes

Reaction equation

HRID 982268 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]([CH3:31])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]([OH:24])[CH2:22][N:23]=2)=[CH:14][CH:13]=1>ClCCCl>[CH3:10][N:11]([CH3:31])[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[O:19][CH:20]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:21]([O:24][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:22][N:23]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650624HCID 14650624, compound

Product 1

HCID 14650711HCID 14650711, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (0.49 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-2-[4-(dimethylamino)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1 g) in 1,2-dichloroethane (12 cc). The solution obtained is heated to reflux for 2 hours and then concentrated to dryness under reduced pressure (2.7 kPa), The residue is purified by chromatography on silica (0.063-0.02 mm; 50 g) contained in a column 2.5 cm in diameter (eluent: cyclohexane/ethyl acetate (7:3 by volume)]collecting 20-cc fractions. Fractions 9 to 15 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diethyl ether, (5RS, 6SR)-2-[4-(dimethylamino)phenyl]-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.55 g), m.p. 183° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 2 hours
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is purified by chromatography on silica (0.063-0.02 mm; 50 g)
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallization in diethyl ether

Sources & evidence

ORD record
ord-55424041ec804fbaac7d910f7fc382fd
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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