Phenyl isocyanate → HCID 67928889, compound

HRID 982274Notes

Reaction equation

HRID 982274 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([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)(=[O:12])[CH3:11]>O1CCCC1>[C:10]([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)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67928884HCID 67928884, compound

Product 1

HCID 67928889HCID 67928889, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Phenyl isocyanate (0.95 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-acetylphenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (2 g) in tetrahydrofuran (25 cc). The solution obtained is heated to 50° C. for 5 hours and then concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization in ethanol, (5RS, 6SR)-2-(4-acetylphenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (1.9 g), m.p. 168° C., is obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-282d629bc1b240388fb05261088b4af2
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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