Water → HCID 21107908, compound

HRID 1765967Notes

Reaction equation

HRID 1765967 reaction equation
[C:1]1([C:7]2[C:15]3[N:14]=[C:13]([CH:16]=[O:17])[NH:12][C:11]=3[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[CH3:24][N:12]1[C:11]2[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:9][CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]=2[N:14]=[C:13]1[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 21107911HCID 21107911, compound

Product 1

HCID 21107908HCID 21107908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.3 g (11.07 mmol) 4,7-diphenyl-1H-benzimidazole-2-carbaldehyde, 8.60 g (62.0 mmol) anhydrous K2CO3 and 1.1 ml (11.07 mmol) dimethyl sulfate in 30 ml anhydrous DMF was stirred at room temperature for 30 min. The reaction mixture was then poured into 300 ml water, stirred for 10 min and extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (3×50 ml) and dried over anhydrous Na2SO4. The solvent was evaporated to give an yellow oil which was triturated with 20 ml methanol at 0° C., filtered while cold, washed with cold (0° C.) methanol (2×10 ml) and dried under reduced pressure. Yield 3.1 g (89.6%). 1H NMR (250 MHz, CDCl3), δ, ppm: 3.74 (s, 3H), 7.47 (m, 10H) 8.04 (d, JHH=7.8 Hz, 2H), 10.1 (s, 1H).

Workup

  1. stirringstirred for 10 min
  2. extractionextracted with dichloromethane (3×100 ml)
  3. washThe combined extracts were washed with water (3×50 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customto give an yellow oil which
  7. customwas triturated with 20 ml methanol at 0° C.
  8. filtrationfiltered while cold,
  9. washwashed with cold (0° C.) methanol (2×10 ml)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-b80f2e117e0c4452bfd4182ed4a7f13e
Source dataset
uspto-grants-2007_06
Patent number
US07229943B2

Reaction notes

Loading…