3,4-Dichlorophenyl isocyanate → HCID 14650637, compound

HRID 982238Notes

Reaction equation

HRID 982238 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[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>[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 14650590HCID 14650590, compound

Product 1

HCID 14650637HCID 14650637, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,4-Dichlorophenyl isocyanate (1.15 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 (1.52 g) in 1,2-dichloroethane (20 cc). The solution obtained is heated to reflux for 6 hours and then concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization in acetonitrile, (4RS, 5RS)-5-(3,4-dichlorophenylcarbamoyloxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazine (2 g), m.p. 184° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 6 hours
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-936bcf4bf7ca473aa886a94c754fadd2
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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