Phenyl isocyanate → HCID 14650707, compound

HRID 982267Notes

Reaction equation

HRID 982267 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+: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])=[O:11]>ClCCCl>[N+: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])=[O:11]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650620HCID 14650620, compound

Product 1

HCID 14650707HCID 14650707, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (1.6 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, o[(5RS, 6SR)-2-(4-nitrophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (4.1 g) in 1,2-dichloroethane (45 cc). The solution obtained is heated to 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; 100 g) contained in a column 2.5 cm in diameter [eluent: dichloromethane/methanol (97:3 by volume)], collecting 20-cc fractions. Fractions 10 to 31 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in acetonitrile, (5RS, 6SR)-2-(4-nitrophenyl)-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (1.35 g), m.p. 170° C., is obtained.

Workup

  1. temperaturemaintained under an argon atmosphere
  2. customThe solution obtained
  3. temperatureis heated
  4. temperatureto reflux for 4 hours
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 100 g)
  7. customcollecting 20-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-e23484bb4c91466d86f8dd00bad3f9d2
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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