Sodium Hydroxide → 2-[[(3,5-Dimethyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

HRID 35483ノート

反応式

HRID 35483 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 212958802-[[(3,5-Dimethyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-475d9f3e8664440cb6de298f9aee601d
出典データセット
uspto-grants-1988_08
特許番号
US04766133

反応ノート

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