Benzimidazole → HCID 20506265, compound

HRID 354927Notes

Reaction equation

HRID 354927 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+].Br[CH2:13][CH:14]([CH3:17])[CH2:15][Cl:16]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[Cl:16][CH2:15][CH:14]([CH3:17])[CH2:13][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 955661-Bromo-3-chloro-2-methylpropane

Product 1

HCID 20506265HCID 20506265, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred and warm (40° C.) mixture of 9.5 parts of 1H-benzimidazole, 2 parts of N,N,N-triethylbenzenemethanaminium chloride, 225 parts of a sodium hydroxide solution 50% and 90 parts of tetrahydrofuran are added 17 parts of 1-bromo-3-chloro-2-methylpropane. The whole is heated to about 60° C. and stirring is continued for 15 minutes at this temperature. The reaction mixture is cooled and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 1-(3-chloro-2-methylpropyl)-1H-benzimidazole as an oily residue.

Workup

  1. temperaturewarm
  2. stirringstirring
  3. temperatureThe reaction mixture is cooled
  4. extractionthe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated

Sources & evidence

ORD record
ord-f5b75cce4af04b569c85e52f0ac97663
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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