Benzene, 1-chloro-3-isocyanato- → HCID 14650643, compound

HRID 982240Notes

Reaction equation

HRID 982240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=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:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 14650590HCID 14650590, compound

Product 1

HCID 14650643HCID 14650643, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3- Chlorophenyl isocyanate (0.8 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). The residue is purified by chromatography on silica (0.063-0.2 mm; 40 g) contained in a column 2 cm in diameter, collecting 15-cc fractions. Fractions 1 to 3, 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 acetonitrile, (4RS, 5RS)-5-(3-chlorophenylcarbamoyloxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazine (1.4 g), m.p. 160° 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. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 40 g)
  6. customcollecting 15-cc fractions
  7. washFractions 1 to 3, eluted with a mixture of ethyl acetate and cyclohexane (3:7 by volume)
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-14d67cade380466f890befacb3691fa1
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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