Benzimidazole → Benzimidazole, 1-(4-chlorobutyl)-

HRID 1482643Notes

Reaction equation

HRID 1482643 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 583170Benzimidazole, 1-(4-chlorobutyl)-Yield 60%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

1H-benzimidazole (11.8 g, 0.10 mol) was dissolved into 200 ml of 20% wt. sodium hydroxide, 4-chlorobromobutane (34.3 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 12.5 g of 1-(4-chlorobutyl)-1H-benzimidazole, with a yield of 60.0%.

Workup

  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

Sources & evidence

ORD record
ord-4bcaf1a20aec4b7997c5b48d8de57c70
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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