Potassium Carbonate → 2-[[(4 Ethoxy-3-methyl-2-pyridyl) methyl]thio]-5-(trifluoromethyl)benzimidazole

HRID 1709771Notes

Reaction equation

HRID 1709771 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH3:12])[CH:6]=[CH:5][N:4]=1.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[NH:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S:22][C:20]2[NH:21][C:17]3[CH:16]=[C:15]([C:14]([F:26])([F:25])[F:13])[CH:24]=[CH:23][C:18]=3[N:19]=2)[C:8]=1[CH3:9])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107261912-(Chloromethyl) 4-ethoxy-3-methylpyridineHCID 178506086HCID 178506086, compound

Product 1

HCID 230365182-[[(4 Ethoxy-3-methyl-2-pyridyl) methyl]thio]-5-(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5 g of 2-(chloromethyl) 4-ethoxy-3-methylpyridine and 5 g of 5-(trifluoromethyl) 2 benzimidazolethiol in 130 ml of abs. acetone was treated with 5 g of finely ground potassium carbonate and stirred at room temperature under argon for 2 hours. 100 ml of acetone were distilled off in a vacuum, whereupon the remaining portion of the reaction mixture was poured onto ice The crystallized-out product was filtered off and dissolved in methylene chloride. The solution obtained was washed with water, dried and concentrated. The residue was chromatographed on silica gel while eluting using methylene chloride and methylene chloride/ethyl acetate (1:1), with the medium pressure flash chromatography method. 2-[[(4 ethoxy-3-methyl-2-pyridyl) methyl]thio]-5-(trifluoromethyl)benzimidazole which melts at 173°-177° was obtained after recrystallization from ethyl acetate/ether.

Workup

  1. distillation100 ml of acetone were distilled off in a vacuum, whereupon the remaining portion of the reaction mixture
  2. additionwas poured onto ice The crystallized-out product
  3. filtrationwas filtered off
  4. dissolutiondissolved in methylene chloride
  5. customThe solution obtained
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel
  10. washwhile eluting

Sources & evidence

ORD record
ord-22ce7d2254e94465a87ff3026e8c9f6e
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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