1-Bromo-3-chloropropane → 1-(3-chloropropyl)-2-methyl-1H-benzimidazole

HRID 1482576

反応式

HRID 1482576 の反応式
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:13][CH2:14][CH2:15][CH2:16][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1]

参加物

6

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 119842-MethylbenzimidazoleHCID 14798Sodium Hydroxide

生成物 1

HCID 212393601-(3-chloropropyl)-2-methyl-1H-benzimidazole収率 62.1%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
60 °C

実験手順

2-methyl-1H-benzimidazole (13.2 g, 0.10 mol) was dissolved into 200 ml of 20% wt. sodium hydroxide, 3-chlorobromopropane (31.4 g, 0.20 mol) and tetrabutyl ammonium bromide (1.0 g) were added, and mixed for 5 min. The mixture was heated to 60° C., stirred to react for 2 hours. Then the reaction solution was cooled down to ambient temperature, 100 ml of dichloromethane was added for extraction and liquid separation. To the aqueous phase, 100 of dichloromethane was added for extraction. Organic phases were mixed, washed with 100 ml of saturated saline. Liquid was separated, and organic phase was evaporated to dryness to produce oily product. Oily products were separated and purified by chromatography with neutral Al2O3 to produce 12.9 g of 1-(3-chloropropyl)-2-methyl-1H-benzimidazole, with a yield of 62.1%.

後処理

  1. additionwere added
  2. additionmixed for 5 min
  3. customto react for 2 hours
  4. temperatureThen the reaction solution was cooled down to ambient temperature
  5. additionOrganic phases were mixed
  6. washwashed with 100 ml of saturated saline
  7. customLiquid was separated
  8. customorganic phase was evaporated to dryness
  9. customto produce oily product
  10. customOily products were separated
  11. custompurified by chromatography with neutral Al2O3

出典と根拠

ORDレコード
ord-a52e6e614df043b19ce775c816ab460d
出典データセット
uspto-grants-2016_08
特許番号
US09415047B2

関連ノート

読み込み中…