Methyl iodide → HCID 18763063, compound

HRID 431076Notes

Reaction equation

HRID 431076 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][C:22](=O)C(F)(F)F)=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].CI>CS(C)=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18762988HCID 18762988, compound

Product 1

HCID 18763063HCID 18763063, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

11.2 g (30.0 mmol) of N-{2-[2-(4-cyanophenyl)-ethyl]-1-methyl-benzimidazol-5-yl}-trifluoroacetamide, 10.5 g (76.0 mmol) of potassium carbonate and 2.0 mL of methyliodide were stirred for 3 hours in 80 mL of dimethylsulphoxide at 40-50° C. Then the mixture was diluted with 100 mL of ethyl acetate, poured onto water and extracted. The organic phase is again washed with water, dried and concentrated by evaporation. The residue is chromatographed on silica gel. The methylated trifluoroacetamide is taken up in MeOH, with 10 mL of conc. aqueous ammonia solution and stirred for 4 h at 30-40° C. The methanol is distilled off, the residue is taken up in 75 mL of ethyl acetate, washed with water, dried and evaporated down. The product is crystallised from diethylether.

Workup

  1. additionpoured onto water
  2. extractionextracted
  3. washThe organic phase is again washed with water
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel
  7. distillationThe methanol is distilled off
  8. washwashed with water
  9. customdried
  10. customevaporated down
  11. customThe product is crystallised from diethylether

Sources & evidence

ORD record
ord-090e11ba6e914eea8cee39666c83e6b7
Source dataset
uspto-grants-2003_12
Patent number
US06656956B2

Reaction notes

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