Sodium Hydroxide → HCID 118386885, compound

HRID 1482587Notes

Reaction equation

HRID 1482587 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[CH:11][NH:10][C:9]=2[CH:13]=1)=[O:4].[OH-].[Na+].[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][N:10]1[C:9]2[CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][C:8]=2[N:12]=[CH:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 2779733methyl 1H-1,3-benzodiazole-5-carboxylate

Product 1

HCID 118386885HCID 118386885, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-methoxycarbonyl-1H-benzimidazole (17.6 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 16.9 g of 1-(4-chlorobutyl)-6-methoxycarbonyl-1H-benzimidazole, with a yield of 63.4%.

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-2ba2b4ee26bd47a9aeb78bab27c7ef4c
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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