Dimethylformamide dimethyl acetal → HCID 178483563, compound

HRID 910245Notes

Reaction equation

HRID 910245 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CN(C)C=O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7]([C:9]3[CH:10]=[CH:11][C:12]([C:15](=[O:17])/[CH:16]=[CH:22]/[N:23]([CH3:25])[CH3:24])=[CH:13][CH:14]=3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178466112HCID 178466112, compound

Product 1

HCID 178483563HCID 178483563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Subsequently, 1-[4-(5-bromo-1H-benz[d]imidazol-2-yl)phenyl]-1-ethanone (592 mg) and N,N-dimethylformamide dimethyl acetal (468 μL) were dissolved in N,N-dimethylformamide (10 mL), followed by heating at 100° C. for 2 hours. The reaction mixture was concentrated, and the residue was subjected to flash chromatography. Fraction eluted by dichloromethane-methanol (15:1) were concentrated under reduced pressure, followed by recovering the solid through filtration by use of isopropyl ether, to thereby yield a 1:1 mixture (116 mg) of (E)-1-[4-(5-bromo-1H-benz[d]imidazol-2-yl)phenyl]-3-dimethylamino-2-propen-1-one and (E)-1-[4-(6-bromo-1H-benz[d]imidazol-2-yl)phenyl]-3-dimethylamino-2-propen-1-one.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washFraction eluted by dichloromethane-methanol (15:1)
  3. concentrationwere concentrated under reduced pressure
  4. customby recovering the solid
  5. filtrationthrough filtration by use of isopropyl ether

Sources & evidence

ORD record
ord-1a1501ed1ec34c4ca66e04af1df1ae0e
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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