Sodium Hydroxide → HCID 118386889, compound

HRID 1482585Notes

Reaction equation

HRID 1482585 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][N:7]1[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 785995-Chloro-1H-benzimidazoleHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 118386889HCID 118386889, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-chloro-1H-benzimidazole (15.2 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 15.1 g of 1-(4-chlorobutyl)-6-chloro-1H-benzimidazole, with a yield of 62.3%.

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-01f7233b61fa4532bdc5c71dcd73f5ad
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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