HCID 178520865, compound → HCID 178519575, compound

HRID 658099Notes

Reaction equation

HRID 658099 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:30])[C:10](=[C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[NH:22]2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>[O-2].[O-2].[Mn+4].ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:30])[C:10](=[C:21]2[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[NH:25]2)[C:11]([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH:19]=[O:20])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 178520865HCID 178520865, compound

Product 1

HCID 178519575HCID 178519575, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A 13.55 g portion of manganese dioxide was added to 20 ml of dichloromethane solution containing 2.11 g of 1-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-[3-(hydroxymethyl)phenyl]propane-1,3-dione and stirred for 4.5 hours. After celite filtration and concentration, the thus formed residue was crystallized from hexane-ethyl acetate to obtain 1.09 g (52%) of 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]benzaldehyde (Reference Example 10-1). FA: 405

Workup

  1. filtrationAfter celite filtration and concentration
  2. customthe thus formed residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1055e9160b4549ad90a020f6c918d630
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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