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

HRID 1709769Notes

Reaction equation

HRID 1709769 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([N+:10]([O-:12])=[O:11])[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>[CH3:9][C:8]1[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)=[N:4][CH:5]=[CH:6][C:7]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 160959042-(Chloromethyl)-3-methyl-4-nitropyridineHCID 178506086HCID 178506086, compound

Product 1

HCID 230364992-[[(3-Methyl-4-nitro 2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 9.4 g of 2-(chloromethyl)-3-methyl-4-nitropyridine and 10 g of 5-(trifluoromethyl)-2-benzimidazolethiol in 260 ml of abs. acetone was treated with 3 g of finely ground potassium carbonate and stirred at room temperature under argon for 18 hours. 180 ml of acetone were distilled off in a vacuum, whereupon the remaining portion of the reaction mixture was poured on to ice. The crystallized-out product was filtered off and dried at 35° in a drying oven By recrystallization from ethyl acetate/n-hexane there was obtained 2-[[(3-methyl-4-nitro 2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole of melting point 192°-193°.

Workup

  1. distillation180 ml of acetone were distilled off in a vacuum, whereupon the remaining portion of the reaction mixture
  2. additionwas poured on to ice
  3. filtrationThe crystallized-out product was filtered off
  4. dry with materialdried at 35° in a drying oven By recrystallization from ethyl acetate/n-hexane there

Sources & evidence

ORD record
ord-723fb6bb14e74e0091b3883e992ce6aa
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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