Acetone → HCID 178467978, compound

HRID 658097Notes

Reaction equation

HRID 658097 reaction equation
C1COCC1.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[C:15]([C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)=[O:27])[C:16]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:22])=[O:17].[Cl-].[NH4+].[CH3:37][C:38]([CH3:40])=[O:39]>>[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[C:15]([C:16]([C:18]1[CH:25]=[CH:24][CH:23]=[C:20]([CH:21]([OH:22])[CH2:37][C:38](=[O:39])[CH3:40])[CH:19]=1)=[O:17])[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)=[O:27]

Participants

5

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178519574HCID 178519574, compound

Product 1

HCID 178467978HCID 178467978, compoundYield 53%

Procedure

At −78° C., 1.0 M sodium hexamethylenedisilazane-THF solution was added dropwise to 10 ml of THF solution containing 300 mg of 3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]benzaldehyde and 69 μl of acetone and stirred for 15 minutes. This was mixed with appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 184 mg (53%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(1-hydroxy-3-oxobutyl)phenyl]propane-1,3-dione (Reference Example 7-1) from a hexane-ethyl acetate (2:1-1:2) eluate. ES+: 445

Workup

  1. custompurified water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-895384fec2f74392803efeea1a5ec1d8
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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