1-Bromo-3-chloropropane → 1-(3-chloropropyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

HRID 126854Notes

Reaction equation

HRID 126854 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:11].[OH-].[Na+].Br[CH2:15][CH2:16][CH2:17][Cl:18]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:18][CH2:17][CH2:16][CH2:15][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:2]([CH3:1])[C:3]1=[O:11]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

Product 1

HCID 133608921-(3-chloropropyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 47 parts of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 375 parts of a sodium hydroxide solution 50% are added 96 parts of 1-bromo-3-chloropropane at 60° C. The whole is heated to 70° C. and stirring is continued for 1 hour at 70° C. The reaction mixture is poured onto crushed ice and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated, yielding 80 parts of 1-(3-chloropropyl)-1,3-dihydro-3-methyl-2H-benzimidazol-2-one as an oily residue.

Workup

  1. additionThe reaction mixture is poured
  2. customonto crushed ice
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8606ea1e294b4b87a4415b27c6fce2e0
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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