4-Chlorophenyl Isocyanate → HCID 14650645, compound

HRID 982241Notes

Reaction equation

HRID 982241 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[C:11]1([C:17]2[O:18][CH2:19][CH:20]([OH:29])[CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:29][CH:20]2[CH2:19][O:18][C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:22][CH:21]2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 14650590HCID 14650590, compound

Product 1

HCID 14650645HCID 14650645, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Chlorophenyl 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 (1.2 g) in 1,2-dichloroethane (20 cc). The solution obtained is heated to reflux for 7 hours 30 minutes and then concentrated to dryness under reduced pressure (2.7 kPa). After two successive recrystallizations in acetonitrile, (4RS, 5RS)-5-(4-chlorophenylcarbamoyloxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazine (1.1 g), m.p. 200° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 7 hours 30 minutes
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customAfter two successive recrystallizations in acetonitrile

Sources & evidence

ORD record
ord-6e4d20f8538f4a05ac761222283a6e5e
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

Loading…