3-(Chloromethyl)pyridine hydrochloride → 1,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-one

HRID 2051686Notes

Reaction equation

HRID 2051686 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].C[O-].[Na+].Cl.Cl[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:3]1=[O:11]

Participants

5

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneHCID 10942334Sodium Methoxide

Product 1

HCID 203795071,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-oneYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 25 parts of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one, 64 parts of sodium methanolate solution 30% and 240 parts of methanol is stirred for one hour at room temperature. Then there are added 27.88 parts of 3-(chloromethyl)pyridine hydrochloride and stirring is continued for 3 hours at reflux temperature. The reaction mixture is cooled and the formed precipitate (sodium chloride) is filtered off. The filtrate is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 16 parts (39.3%) of 1,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-one; mp. 90° C.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. filtrationthe formed precipitate (sodium chloride) is filtered off
  6. customThe filtrate is evaporated
  7. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-86797b99b53046ce8f395c0a8afc5aff
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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