Thionyl Chloride → (+/-)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

HRID 346994Notes

Reaction equation

HRID 346994 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:33])([C:25]4[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=4)[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]([CH3:34])[C:10](=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:38])=O>>[Cl:38][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:18]([OH:33])([C:19]2[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=2)[C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[N:11]([CH3:34])[C:10](=[O:35])[CH:9]=[C:8]3[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10140969(+/-)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone

Product 1

HCID 21082106(+/-)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinoneYield 100%

Procedure

A mixture of (±)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5yl)methyl]-1-methyl-2(1H)-quinolinone (described in Example B9) (0.000823 mol) in thionyl chloride (4 ml) was kept at room temperature for 2 hours. The solvent was evaporated till dryness. The residue was taken up in H2O. EtOAc was added. The mixture was basified with K2CO3 (10%) and extracted. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding 0.43 g (>100%) of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinone.

Workup

  1. customThe solvent was evaporated till dryness
  2. additionEtOAc was added
  3. extractionextracted
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a9bc77218d9945d6a627b68c02f400af
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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