1,6-Dichlorohexane → 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

HRID 2050243Notes

Reaction equation

HRID 2050243 reaction equation
[H-].[Na+].[CH3:3][C:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])=[CH2:5].[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Cl>CN(C)C=O>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]([C:4]([CH3:3])=[CH2:5])[C:7]1=[O:15]

Participants

5

Reactant 3

HCID 165511,6-DichlorohexaneHCID 24758Sodium hydrideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 205063391-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 3.2 parts of a sodium hydride dispersion 70% in 9 parts of N,N-dimethylformamide is added dropwise (slowly), during a 2 hours-period, a mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 77.5 parts of 1,6-dichlorohexane and 36 parts of N,N-dimethylformamide. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is filtered over hyflo and the N,N-dimethylformamide is evaporated in vacuo. The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet. The residue is dissolved in methylbenzene and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the filtrate is evaporated, yielding 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue.

Workup

  1. additionis added dropwise (slowly), during a 2 hours-period
  2. filtrationThe reaction mixture is filtered over hyflo
  3. customthe N,N-dimethylformamide is evaporated in vacuo
  4. distillationThe excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet
  5. dissolutionThe residue is dissolved in methylbenzene
  6. stirringthe solution is stirred with activated charcoal
  7. filtrationThe latter is filtered off over hyflo
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-b43fba3da3a24b8985c36d2e9025803d
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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