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

HRID 354926Notes

Reaction equation

HRID 354926 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 and 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 and methanol (90:10) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-0082493394944c15b79fd648eac874c6
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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