Sodium Hydroxide → 1-(4-chlorobutyl)-6-cyano-1H-benzimidazol

HRID 1482586Notes

Reaction equation

HRID 1482586 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][NH:8][C:7]=2[CH:11]=1)#[N:2].[OH-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18][N:8]1[C:7]2[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 2239061H-Benzimidazole-6-carbonitrile

Product 1

HCID 1183869301-(4-chlorobutyl)-6-cyano-1H-benzimidazolYield 63.1%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-cyano-1H-benzimidazole (14.3 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. Post treatment was performed based on common method one for synthesis. Oily products were separated and purified by chromatography with neutral Al2O3 to produce 14.7 g of 1-(4-chlorobutyl)-6-cyano-1H-benzimidazole, with a yield of 63.1%.

Workup

  1. additionwere added
  2. additionmixed for 5 min
  3. customto react for 2 hours
  4. customPost treatment was performed based on common method one for synthesis
  5. customOily products were separated
  6. custompurified by chromatography with neutral Al2O3

Sources & evidence

ORD record
ord-484e471c2da24cc9a6919d8aaffbe575
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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