Phenyl isocyanate → HCID 67928887, compound

HRID 982280Notes

Reaction equation

HRID 982280 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]([OH:16])[CH2:14][N:15]=2)=[CH:6][CH:5]=1)[CH3:2].[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCCl>[CH2:1]([S:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]([O:16][C:30](=[O:31])[NH:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][N:15]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67928883HCID 67928883, compound

Product 1

HCID 67928887HCID 67928887, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (5RS, 6SR)-2-[4-(ethylthio)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (6.5 g) and phenylisocyanate (2.6 g) in 1,2-dichloroethane (100 cc) is heated to a temperature in the region of 80° C. for 5 hours. After being cooled, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue obtained is purified by chromatography on silica (0.063-0.2 mm; 150 g) contained in a column 3.5 cm in diameter eluting in 20-cc fractions with an ethylacetate/cyclohexane mixture (50:50 by volume). Fractions 5 to 15 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is further purified by chromatography on silica (0.063-0.2 mm; 100 g) contained in a column 3.5 cm in diameter, eluting in 25-cc fractions with a methylene chloride/methanol mixture (99:1 by volume). Fractions 10 to 18 are combined and concentrated to dryness under reduced pressure. (5RS, 6SR)-2-[4-(Ethylthio)phenyl]-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (1.1 g), m.p. 70° C., is thereby obtained.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customthe residue obtained
  4. customis purified by chromatography on silica (0.063-0.2 mm; 150 g)
  5. washeluting in 20-cc fractions with an ethylacetate/cyclohexane mixture (50:50 by volume)
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue obtained
  8. customis further purified by chromatography on silica (0.063-0.2 mm; 100 g)
  9. washeluting in 25-cc fractions with a methylene chloride/methanol mixture (99:1 by volume)
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b5b96a9bcdf042dbbf220d8cc7d25ef7
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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