1-Bromo-3-chloropropane → 1-(3-chloropropyl)-1,3-dihydro-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]([CH3:13])=[CH2:12])[C:6]=2[CH:14]=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:9]1[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:6]=2[N:7]([C:11]([CH3:13])=[CH2:12])[C:8]1=[O:10]Participants
Conditions
- Temperature
- 60 °C
Procedure
To a stirred and hot (50° C.) mixture of 47 parts of 1,3-dihydro-6-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one and 5 parts of N,N,N-triethylbenzenemethanaminium chloride in 300 parts of a sodium hydroxide solution 50% are added 79 parts of 1-bromo-3-chloropropane. The whole is heated to 60° C.: exothermic reaction (temperature rises to 75° C.). Stirring is continued for one hour while cooling to keep the temperature between 60° and 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 1-(3-chloropropyl)-1,3-dihydro-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one; bp. 140° C. at 0.015 mm. pressure.
Workup
- customexothermic reaction (temperature rises to 75° C.)
- stirringStirring
- temperaturewhile cooling
- customthe temperature between 60° and 70° C
- temperatureThe reaction mixture is cooled
- additionpoured
- customonto crushed ice
- extractionThe product is extracted with methylbenzene
- washThe extract is washed three times with water
- customdried
- filtrationfiltered
- customevaporated
- distillationThe oily residue is distilled
Sources & evidence
- ORD record
- ord-31ed76a0bfa54338b92308222115c739
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377578
Reaction notes
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