Phenyl isocyanate → HCID 86744629, compound

HRID 982277Notes

Reaction equation

HRID 982277 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]([OH:21])[CH2:19][N:20]=2)=[CH:11][CH:10]=1)[C:3](=[O:8])[C:4]([F:7])([F:6])[F:5].[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCCl>[CH3:1][N:2]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][CH:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]([O:21][C:35](=[O:36])[NH:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:19][N:20]=2)=[CH:13][CH:14]=1)[C:3](=[O:8])[C:4]([F:5])([F:7])[F:6]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86744630HCID 86744630, compound

Product 1

HCID 86744629HCID 86744629, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (5RS, 6SR)-2-[4-(N-methyltrifluoroacetamido)phenyl]-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.54 g) and phenyl isocyanate (0.6 g) in 1,2-dichloroethane (25 cc) is heated to reflux for 18 hours. The reaction mixture is then concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization of the residue thereby obtained in isopropyl ether, (5RS, 6SR)-2-[4-(N-methyltrifluoroacetamido)phenyl]-6-phenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.77 g), m.p. 160° C., is obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 18 hours
  3. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure (2.7 kPa)
  4. customAfter recrystallization of the residue
  5. customthereby obtained in isopropyl ether

Sources & evidence

ORD record
ord-7cf5206e500b42c3832000eb8beb028c
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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