Benzimidazole → HCID 57475148, compound

HRID 1095535Notes

Reaction equation

HRID 1095535 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1>O1CCOCC1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[CH:14]2)=[CH:5]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 57475148HCID 57475148, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-1H-indole (4.48 g, 20 mmol) and benzimidazole (4.72 g, 40 mmol) in abs. dioxane (50 ml) was stirred at 90° C. for 13 h. The solvent was then removed i. vac., CHCl3 (200 ml) was added to the residue and the mixture was washed twice with water. The organic phase was dried over Na2SO4 and concentrated i. vac. and the residue which remained was purified by flash chromatography with CHCl3/MeOH (40:1). Yield: 1.32 g (25%), pale brown solid

Workup

  1. customThe solvent was then removed i
  2. addition, CHCl3 (200 ml) was added to the residue
  3. washthe mixture was washed twice with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated i
  6. customand the residue which remained was purified by flash chromatography with CHCl3/MeOH (40:1)

Sources & evidence

ORD record
ord-ab119a08a3b5425ca3bdee6736eb2ee7
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…