Ethanol → HCID 58577496, compound

HRID 587478Notes

Reaction equation

HRID 587478 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].CCO.[OH-].[Na+]>O>[Cl:1][C:2]1[N:6]([CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 785722-Chlorobenzimidazole

Product 1

HCID 58577496HCID 58577496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-1H-benzimidazole (6.10 g), bromoacetaldehyde diethyl acetal (7.22 mL), EtOH (70 mL), and 8 M NaOH aqueous solution (10 mL) was refluxed for 3 d. The reaction mixture was poured into water and the mixture was extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography eluting with hexane/AcOEt (10/1) to give 2-chloro-1-(2,2-diethoxyethyl)-1H-benzimidazole (5.50 g).

Workup

  1. temperaturewas refluxed for 3 d
  2. extractionthe mixture was extracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography
  7. washeluting with hexane/AcOEt (10/1)

Sources & evidence

ORD record
ord-599bac38f95448f3bb005d92804522e5
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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