Phenyl isocyanate → HCID 14650693, compound

HRID 982251Notes

Reaction equation

HRID 982251 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][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][O:11][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 14650604HCID 14650604, compound

Product 1

HCID 14650693HCID 14650693, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (1.25 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-methoxyphenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.5 g) in 1,2-dichloroethane (20 cc). The solution obtained is heated to reflux for 6 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by chromatography on silica (0.063-0.2 mm; 50 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate/triethylamine (60:35:5 by volume)], collecting 20-cc fractions. Fractions 4 to 10 are combined and concentrated to dryness under reduced pressure (2. 7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-2-(4-methoxyphenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.52 g), m.p. 223° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 6 hours
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 50 g)
  6. customcollecting 20-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (2. 7 kPa) at 40° C
  8. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-04a775bbb58d46e19886d8eb999b8abd
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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