Phenyl isocyanate → HCID 14650661, compound

HRID 982255Notes

Reaction equation

HRID 982255 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([C:16]2[S:17][CH2:18][CH:19]([OH:28])[CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCCl>[C:10]1([C:16]2[S:17][CH2:18][CH:19]([O:28][C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:21]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650629HCID 14650629, compound

Product 1

HCID 14650661HCID 14650661, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenyl isocyanate (1.1 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-thiazin-5-ol (0.86 g) in 1,2-dichloroethane (10 cc). The solution obtained is stirred under reflux for 3 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is then stirred with a mixture of ethyl acetate and cyclohexane (1:4 by volume). An insoluble precipitate is separated by filtration and the filtrate concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization in diisopropyl ether, (4RS, 5RS)-2,4-diphenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-thiazine (0.75 g), m.p. 159° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. stirringThe residue is then stirred with a mixture of ethyl acetate and cyclohexane (1:4 by volume)
  5. customAn insoluble precipitate is separated by filtration
  6. concentrationthe filtrate concentrated to dryness under reduced pressure (2.7 kPa)
  7. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-6d96667c022d48d0a821a9718716f509
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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