1-Bromo-3-chloropropane → HCID 20506304, compound

HRID 354925Notes

Reaction equation

HRID 354925 reaction equation
[CH:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O1CCCC1.Br[CH2:24][CH2:25][CH2:26][Cl:27]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.CC1C=CC=CC=1>[Cl:27][CH2:26][CH2:25][CH2:24][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 37587Benzimidazole, 2-cyclohexyl-

Product 1

HCID 20506304HCID 20506304, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 20 parts of 2-cyclohexyl-1H-benzimidazole, 2 parts of N,N,N-triethylbenzenemethanaminium chloride, 225 parts of a sodium hydroxide solution 50% and 140 parts of tetrahydrofuran is stirred and heated to 40° C. Then there are added 31.5 parts of 1-bromo-3-chloropropane and stirring is continued for 15 minutes at 60° C. The reaction mixture is cooled, methylbenzene is added and the layers are separated. The aqueous phase is extracted with methylbenzene. The combined methylbenzene-phases are washed with water, dried, filtered and evaporated. The 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-chloropropyl)-2-cyclohexyl-1H-benzimidazole as an oily residue.

Workup

  1. stirringstirring
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. extractionThe aqueous phase is extracted with methylbenzene
  5. washThe combined methylbenzene-phases are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

Sources & evidence

ORD record
ord-c07f041569c048339fb2047f5558349f
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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