18-Crown-6 → 1-(2-Chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile

HRID 276038ノート

反応式

HRID 276038 の反応式
[O-][C:2]#[N:3].[K+].C1OCCOCCOCCOCCOCCOC1.[Cl:23][C:24]1[CH:42]=[CH:41][CH:40]=[CH:39][C:25]=1[CH2:26][N:27]1[C:31]2[CH:32]=[C:33]([CH2:36]Cl)[CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH3:38]>CS(C)=O>[Cl:23][C:24]1[CH:42]=[CH:41][CH:40]=[CH:39][C:25]=1[CH2:26][N:27]1[C:31]2[CH:32]=[C:33]([CH2:36][C:2]#[N:3])[CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH3:38]

参加物

5

反応物 3

HCID 2855718-Crown-6HCID 11378442Potassium cyanateHCID 226203421h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-

生成物 1

HCID 186809811-(2-Chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile収率 43%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Potassium cyanate (0.450 g) and 0.450 g of 18-crown-6 were added to a solution of 1.20 g of 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole in 10 ml of dimethylsulfoxide, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was extracted with the addition of chloroform, water and a small amount of aqueous ammonia. The organic layer was concentrated, and the residue was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 20:1) to give 0.500 g of 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile.

後処理

  1. extractionThe reaction mixture was extracted with the addition of chloroform, water
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified through silica-gel column chromatography (eluent
  4. additiona mixture of chloroform and methanol at a ratio of 20:1)

出典と根拠

ORDレコード
ord-4ec5c6e3e3b14b689ae0ae8c0e55b205
出典データセット
uspto-grants-2002_03
特許番号
US06352985B1

反応ノート

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