Sodium Hydroxide → HCID 21295880, compound

HRID 35483Notes

Reaction equation

HRID 35483 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.Cl.Cl[CH2:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][N:19]=1.[OH-].[Na+]>O>[CH3:24][C:23]1[C:18]([CH2:17][S:10][C:8]2[NH:9][C:5]3[CH:4]=[C:3]([C:2]([F:13])([F:1])[F:14])[CH:12]=[CH:11][C:6]=3[N:7]=2)=[N:19][CH:20]=[C:21]([CH3:25])[CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 212733342-(Chloromethyl)-3,5-dimethylpyridine--hydrogen chloride (1/1)HCID 178506086HCID 178506086, compound

Product 1

HCID 21295880HCID 21295880, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.54 g of 5-(trifluoromethyl)-2-benzimidazolethiol are suspended in 400 ml of alcohol and treated with 5.76 g of 2-chloromethyl-3,5-dimethylpyridine hydrochloride while cooling with ice. Thereafter, a solution of 2.4 g of sodium hydroxide in 100 ml of water is added dropwise thereto, the mixture is left to boil at reflux overnight and subsequently evaporated to dryness in vacuo. The residue is dissolved in 800 ml of methylene choride. The solution is washed firstly with 200 ml of 1.5N sodium hydroxide solution and then 3×with 250 ml of water, dried over sodium sulphate and evaporated in vacuo. The crude product is purified on 110 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent. Crystallization from methylene chloride/petroleum ether gives 2-[[(3,5-dimethyl-2 -pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole of melting point 137°-138°.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe mixture is left
  3. temperatureat reflux overnight
  4. customsubsequently evaporated to dryness in vacuo
  5. dissolutionThe residue is dissolved in 800 ml of methylene choride
  6. washThe solution is washed firstly with 200 ml of 1.5N sodium hydroxide solution
  7. dry with material3×with 250 ml of water, dried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe crude product is purified on 110 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent
  10. customCrystallization from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-475d9f3e8664440cb6de298f9aee601d
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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