5-bromo-4-chloro-2-ethyl-1H-benzimidazole → 4-chloro-2-ethyl-1H-benzimidazole-5-carbonitrile

HRID 913569ノート

反応式

HRID 913569 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[C:3]=1[Cl:13].[C:14]([Cu])#[N:15]>CN1C(=O)CCC1>[Cl:13][C:3]1[C:4]2[N:8]=[C:7]([CH2:9][CH3:10])[NH:6][C:5]=2[CH:11]=[CH:12][C:2]=1[C:14]#[N:15]

参加物

4

反応物 2

HCID 578001585-bromo-4-chloro-2-ethyl-1H-benzimidazoleHCID 178418546HCID 178418546、化合物

生成物 1

HCID 674049024-chloro-2-ethyl-1H-benzimidazole-5-carbonitrile収率 35.5%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
220 °C

実験手順

5-Bromo-4-chloro-2-ethyl-1H-benzimidazole (0.050 g, 0.192 mmol) and CuCN (0.030 g, 0.576 mmol) were combined in NMP (3 mL) and heated to 220° C. for 20 min in a microwave. The cooled mixture was partitioned between Et2O and water. The organic portion was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.014 g): MS (ESI) m/z 206 (M+1).

後処理

  1. customThe cooled mixture was partitioned between Et2O and water
  2. washThe organic portion was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification (SiO2, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-726f7b16115b4859b4127be5efff1667
出典データセット
uspto-grants-2011_09
特許番号
US08026262B2

反応ノート

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