1-Isocyanato-4-methoxybenzene → HCID 14650639, compound

HRID 982239Notes

Reaction equation

HRID 982239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[C:12]1([C:18]2[O:19][CH2:20][CH:21]([OH:30])[CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([O:30][CH:21]2[CH2:20][O:19][C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:23][CH:22]2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 14650590HCID 14650590, compound

Product 1

HCID 14650639HCID 14650639, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Methoxyphenyl isocyanate (1 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (4RS, 5RS)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.7 g) in 1,2-dichloroethane (20 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; 40 g) contained in a column 2 cm in diameter, collecting 20-cc fractions. Fractions 2 to 6, 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 diisopropyl ether, (4RS, 5RS)-5-(4-methoxyphenylcarbamoyloxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazine (0.7 g), m.p. 140° 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; 40 g)
  5. customcollecting 20-cc fractions
  6. washFractions 2 to 6, 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 diisopropyl ether

Sources & evidence

ORD record
ord-777d20e2df7e402c804b2c0b3263b73a
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

Loading…