1-Bromo-3-chloropropane → HCID 20506303, compound

HRID 2050247Notes

Reaction equation

HRID 2050247 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1)[CH3:2].[OH-].[Na+].Br[CH2:15][CH2:16][CH2:17][Cl:18]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.CC1C=CC=CC=1>[Cl:18][CH2:17][CH2:16][CH2:15][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=[C:3]1[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 158072-Ethylbenzimidazole

Product 1

HCID 20506303HCID 20506303, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred mixture of 29.2 parts of 2-ethyl-1H-benzimidazole, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 300 parts of a sodium hydroxide solution 60% are added 60 parts of 1-bromo-3-chloropropane. The whole is heated to about 65° C. and stirring is continued for 30 minutes at this temperature. Methylbenzene is added and the whole is poured onto water. The organic phase is separated, dried, filtered and evaporated. The residue is purified twice by column-chromatography over silica gel using a mixture of trichloromethane amd methanol (90:10) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 1-(3-chloropropyl)-2-ethyl-1H-benzimidazole as a residue.

Workup

  1. additionthe whole is poured onto water
  2. customThe organic phase is separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified twice by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane amd methanol (90:10) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-9d553fdb40a64c48ab9f19ecd6f1e185
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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