Phenyl isocyanate → HCID 67928891, compound

HRID 982271Notes

Reaction equation

HRID 982271 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]([OH:25])[CH2:23][N:24]=2)=[CH:15][CH:14]=1)[CH3:11]>ClCCCl>[CH2:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:20][CH:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]([O:25][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:23][N:24]=2)=[CH:17][CH:18]=1)[CH3:11]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67928874HCID 67928874, compound

Product 1

HCID 67928891HCID 67928891, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Phenyl isocyanate (0.38 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-ethoxyphenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (0.8 g) in 1,2-dichloroethane (10 cc). The solution obtained is heated to 80° C. for 3 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is purified by chromatography on silica (0.063-0.2 mm; 100 g), contained in a column 2 cm in diameter, collecting 20-cc fractions. Fractions 3 and 4, eluted with a mixture of cyclohexane and ethyl acetate (6:4 by volume), are concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The solid obtained is then purified again by chromatography on silica (0.063-0.2 mm; 100 g), contained in a column 2 cm in diameter, collecting 20-cc fractions. Fractions 5 to 10, eluted with a mixture of cyclohexane, ethyl acetate and triethylamine (65:30:5 by volume), are concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in ethyl acetate, (5RS, 6SR)-2-(4-ethoxyphenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.35 g), m.p. 80° C., is obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe solid obtained
  4. customis purified by chromatography on silica (0.063-0.2 mm; 100 g)
  5. customcollecting 20-cc fractions
  6. washFractions 3 and 4, eluted with a mixture of cyclohexane and ethyl acetate (6:4 by volume)
  7. concentrationare concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customThe solid obtained
  9. customis then purified again by chromatography on silica (0.063-0.2 mm; 100 g)
  10. customcollecting 20-cc fractions
  11. washFractions 5 to 10, eluted with a mixture of cyclohexane, ethyl acetate and triethylamine (65:30:5 by volume)
  12. concentrationare concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  13. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-f3d3b3e068c34479b5668307f51af00e
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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