1-Bromo-3-chloropropane → 1-(3-chloropropyl)-1,3-dihydro-3-(2-propenyl)-2H-benzimidazol-2-one

HRID 46862Notes

Reaction equation

HRID 46862 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])[CH:2]=[CH2:3].[OH-].[Na+].Br[CH2:17][CH2:18][CH2:19][Cl:20]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:20][CH2:19][CH2:18][CH2:17][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1=[O:13]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 46216401,3-Dihydro-1-(2-propen-1-yl)-2H-benzimidazol-2-one

Product 1

HCID 128917551-(3-chloropropyl)-1,3-dihydro-3-(2-propenyl)-2H-benzimidazol-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred and heated mixture of 17.5 parts of 1,3-dihydro-1-(2-propenyl)-2H-benzimidazol-2-one, 5-parts of N,N,N-triethylbenzenemethanaminium chloride and 150 parts of a sodium hydroxide solution 60% are added dropwise 20.5 parts of 1-bromo-3-chloropropane at 60° C. Upon completion, stirring at 60° C. is continued for 5 hours. The reaction mixture is cooled, water is added and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 21 parts (84%) of 1-(3-chloropropyl)-1,3-dihydro-3-(2-propenyl)-2H-benzimidazol-2-one as a residue.

Workup

  1. temperatureheated
  2. stirringUpon completion, stirring at 60° C.
  3. temperatureThe reaction mixture is cooled
  4. extractionthe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-fb76c28e2c154c6089943d389c04b973
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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