Sodium Hydroxide → 1-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

HRID 46868Notes

Reaction equation

HRID 46868 reaction equation
[CH3:1][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[CH2:3].[OH-].[Na+].Br[CH2:17][CH:18]([CH3:21])[CH2:19][Cl:20]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:20][CH2:19][CH:18]([CH3:21])[CH2:17][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:2]([CH3:1])=[CH2:3])[C:5]1=[O:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 205062821-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-oneYield 90.6%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
55 °C

Procedure

To a stirred mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 5-parts of N,N,N-triethyl benzenemethanaminium chloride and 180 parts of sodium hydroxide solution 60% are added dropwise 21 parts of 1-bromo-3-chloro-2-methylpropane while heating at 55° C. Upon completion, stirring at 55° C. is continued for 3 hours. The reaction mixture is cooled, poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 24 parts (90.6%) of 1-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as a residue.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. extractionthe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b87cf91db1f1412586dd18038036ec83
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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