Phosphorus oxychloride → HCID 22385765, compound

HRID 895149Notes

Reaction equation

HRID 895149 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=O)[CH:13]=[C:12]3[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:14]1[CH:13]=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[CH:10]=2)[N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15484952HCID 15484952, compound

Product 1

HCID 22385765HCID 22385765, compoundYield 85%

Procedure

A mixture of (±)-6-[(4-chlorophenyl)-1H-imidazol-1-ylmethyl]-4phenyl-2(1H)-quinolinone (0.022 mol) in phosphoryl chloride (100 ml) was stirred and refluxed for 2 hours. The mixture was evaporated in vacuo, the residue was taken up in CH2Cl2 and basified with K2CO3 (10%). The organic layer was dried (MgSO4), filtered off and evaporated. The product was used without further purification, yielding 8 g (85%) of (±)-2-chloro-6-[(4-chlorophenyl)-1H-imidazol-1-ylmethyl]-4-phenylquinoline (interm. 5).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe mixture was evaporated in vacuo
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated
  6. customThe product was used without further purification

Sources & evidence

ORD record
ord-cd0a2f01451049b38b362697060f9177
Source dataset
uspto-grants-2005_07
Patent number
US06914066B2

Reaction notes

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