Sodium Iodide → 4-(2,6-Dimethylbenzylamino)-2-methylbenzimidazole

HRID 991589ノート

反応式

HRID 991589 の反応式
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C.C(Cl)Cl.CO>[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 178432166HCID 178432166、化合物

生成物 1

HCID 1784321684-(2,6-Dimethylbenzylamino)-2-methylbenzimidazole収率 30.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

4-amino-2-methylbenzimidazole (6.0 g, 0.041 mol) was dissolved in acetonitrile (120 ml). To the solution were added 2,6-dimethylbenzylchloride (6.3 g, 0.041 mol), sodium carbonate (16 g, 0.15 mol) and a cat. amount of sodium iodide and the reaction mixture was refluxed for 3 h. The sodium carbonate was removed by filtration and was washed with methylene chloride. Vacuum evaporation of the solvent gave an oily residue which was subjected to flash chromatography on silica gel, methylene chloride: methanol (10:1). The residue was crystallized by treating with ethyl acetate to obtain 3.3 g ( 30%) of the title compound.

後処理

  1. customThe sodium carbonate was removed by filtration
  2. washwas washed with methylene chloride
  3. customVacuum evaporation of the solvent
  4. customgave an oily residue which
  5. customThe residue was crystallized
  6. additionby treating with ethyl acetate

出典と根拠

ORDレコード
ord-3cfdfb5136d847588528cfbdbb9bc715
出典データセット
uspto-grants-2002_10
特許番号
US06465505B1

反応ノート

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