Phenyl isocyanate → HCID 14650669, compound

HRID 982247Notes

Reaction equation

HRID 982247 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([C:16]2[O:17][CH:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]([OH:22])[CH2:20][N:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCCl>[C:10]1([C:16]2[O:17][CH:18]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:19]([O:22][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:20][N:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650602HCID 14650602, compound

Product 1

HCID 14650669HCID 14650669, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (0.33 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere of (5RS, 6SR)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (0.4 g) in 1,2-dichloroethane (10 cc). The solution obtained is stirred under reflux for 4 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, collecting 20-cc fractions. Fractions 5 to 11, eluted with a mixture of ethyl acetate and cyclohexane (3:7 by volume), are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in petroleum ether, (5RS, 6SR)-2,6-diphenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.36 g), m.p. 111° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 50 g)
  5. customcollecting 20-cc fractions
  6. washFractions 5 to 11, eluted with a mixture of ethyl acetate and cyclohexane (3:7 by volume)
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customAfter recrystallization in petroleum ether

Sources & evidence

ORD record
ord-68de382eceaf4786a78ca48ba2863a28
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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