Sodium hydride → HCID 54378044, compound

HRID 2051685Notes

Reaction equation

HRID 2051685 reaction equation
C[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].[H-].[Na+].ClC[CH:18]1C[CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19]1>CN(C)C=O>[C:24]1([CH2:23][N:20]2[CH2:19][CH2:18][CH:3]([CH2:2][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[NH:6][C:5]3=[O:13])[CH2:21]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 123645181-Benzyl-3-(chloromethyl)pyrrolidine

Product 1

HCID 54378044HCID 54378044, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred mixture of 43.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one and 270 parts of N,N-dimethylformamide are added portionwise 10 parts of sodium hydride dispersion 60%. After stirring for 1 hour at about 40°-50° C., there are added 53 parts of 3-(chloromethyl)-1-(phenylmethyl)pyrrolidine and the whole is stirred and heated overnight at about 110° C. The reaction mixture is cooled and poured onto water. The product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is taken up in a diluted hydrochloric acid solution and the whole is stirred for 1 hour at room temperature. After cooling, the mixture is alkalized and the product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane with activated charcoal. The latter is filtered off and the filtrate is allowed to crystallize. The product is filtered off and dried, yielding 40 parts (53%) of 1,3-dihydro-1-[1-(phenylmethyl)-3-pyrrolidinylmethyl]-2H-benzimidazol-2-one.

Workup

  1. stirringthe whole is stirred
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted with 4-methyl-2-pentanone
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. stirringthe whole is stirred for 1 hour at room temperature
  13. temperatureAfter cooling
  14. extractionthe product is extracted with 4-methyl-2-pentanone
  15. customThe extract is dried
  16. filtrationfiltered
  17. customevaporated
  18. customThe residue is triturated in 2,2'-oxybispropane with activated charcoal
  19. filtrationThe latter is filtered off
  20. customto crystallize
  21. filtrationThe product is filtered off
  22. customdried

Sources & evidence

ORD record
ord-a57575c3c4724422819dbc3e47cac80f
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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