1-Bromo-3-chloropropane → 3-(3-chloropropyl)-1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one

HRID 258836Notes

Reaction equation

HRID 258836 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:10]([CH3:12])=[CH2:11])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:21][CH2:20][CH2:19][CH2:18][N:8]1[C:4]2[CH:3]=[C:2]([CH3:1])[CH:14]=[CH:13][C:5]=2[N:6]([C:10]([CH3:12])=[CH2:11])[C:7]1=[O:9]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 205062871,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 205063153-(3-chloropropyl)-1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

To a stirred and hot (±50° C) mixture of 34 parts of 1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 300 parts of sodium hydroxide solution 50% are added 57 parts of 1-bromo-3-chloropropane (exothermic reaction: temperature rises to 70° C). The whole is stirred for 1 hour at 65°-70° C. The reaction mixture is cooled and poured onto crushed ice. The product is extracted with methylbenzene. The extract is washed three times with water, dried, filtered and evaporated. The oily residue is distilled yielding 40 parts (84%) of 3-(3-chloropropyl)-1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one; bp. 140° C at 0.02 mm. pressure.

Workup

  1. stirringThe whole is stirred for 1 hour at 65°-70° C
  2. temperatureThe reaction mixture is cooled
  3. additionpoured
  4. customonto crushed ice
  5. extractionThe product is extracted with methylbenzene
  6. washThe extract is washed three times with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-26ddc991bee84baea5c9d9e2a5c411f3
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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