Phosphorus oxychloride → 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine

HRID 1795004Notes

Reaction equation

HRID 1795004 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N+:15]([O-])=[CH:16][CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]=2[C:8]1=[O:26].P(Cl)(Cl)([Cl:38])=O>C(OCC)(=O)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[C:16]([Cl:38])[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]=2[C:8]1=[O:26]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 221793305-[3,5-bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine 10-oxide

Product 1

HCID 221793335-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-[3,5-Bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine 10-oxide (compound of Reference Example 10; 400 mg) was added to phosphorus oxychloride (1.5 mL), and the mixture was refluxed for 1 hour while heated. The solvent was removed by distillation to obtain a residue. To this residue, ethyl acetate was added, and then the resulting crystals were collected. As a result, 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine was obtained (440 mg, 99%).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturewhile heated
  3. customThe solvent was removed by distillation
  4. customto obtain a residue
  5. customthe resulting crystals were collected

Sources & evidence

ORD record
ord-2782e5a7dea645cc9e221e8b7e7e2a76
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

Loading…