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

HRID 913569

반응식

HRID 913569 반응식
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]

참가 물질

4

반응물 2

HCID 578001585-bromo-4-chloro-2-ethyl-1H-benzimidazoleHCID 178418546HCID 178418546, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
220 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-726f7b16115b4859b4127be5efff1667
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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