4-(Trifluoromethyl)phenyl isocyanate → HCID 14650647, compound

HRID 982242Notes

Reaction equation

HRID 982242 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[C:14]1([C:20]2[O:21][CH2:22][CH:23]([OH:32])[CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCCl>[C:14]1([C:20]2[O:21][CH2:22][CH:23]([O:32][C:10](=[O:11])[NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:4][CH:5]=3)[CH:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:25]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 14650590HCID 14650590, compound

Product 1

HCID 14650647HCID 14650647, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(Trifluoromethyl)phenyl 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 (1.26 g) in 1,2-dichloroethane (30 cc). The solution obtained is heated to reflux for 5 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 1 cm in diameter, collecting 20-cc fractions. Fractions 2 and 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 petroleum ether, (4RS, 5RS)-2,4-diphenyl-5-[4-(trifluoromethyl)phenylcarbamoyloxy]-5,6-dihydro-4H-1,3-oxazine (1.4 g), m.p. 140° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 5 hours
  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 20-cc fractions
  7. washFractions 2 and 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 petroleum ether

Sources & evidence

ORD record
ord-0f5d6ee79c564b4da3fa5d0725236082
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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