Benzyl Chloride → HCID 14518676, compound

HRID 1723154Notes

Reaction equation

HRID 1723154 reaction equation
[N:1]1([CH2:6][C:7]2[CH:17]=[CH:16][C:10]3[N:11]([CH3:15])[C:12]([OH:14])=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[N:1]1([CH2:6][C:7]2[CH:17]=[CH:16][C:10]3[N:11]([CH3:15])[C:12](=[O:14])[N:13]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178481591HCID 178481591, compound

Product 1

HCID 14518676HCID 14518676, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4.5 parts of 5-(1H-imidazol-1-ylmethyl)-1-methyl-1H-benzimidazol-2-ol, 0.46 parts of a sodium hydride dispersion 50% and 56 parts of N,N-dimethylformamide was stirred for 30 minutes at 50° C. After the addition of 2.53 parts of (chloromethyl)benzene, the solution was stirred for 2 hours at 50° C. The N,N-dimethylformamide layer was evaporated in vacuo. The residue was diluted with water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 27 parts of ethyl acetate and 44 parts of 2,2'-oxybispropane. The product was filtered off and dried, yielding 5 parts (78.5%) of 1,3-dihydro-5-(1H-imidazol-1-ylmethyl)-1-methyl-3-(phenylmethyl)-2H-benzimidazol-2-one; mp. 129.4° C. (compound 226).

Workup

  1. stirringthe solution was stirred for 2 hours at 50° C
  2. customThe N,N-dimethylformamide layer was evaporated in vacuo
  3. additionThe residue was diluted with water
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 27 parts of ethyl acetate and 44 parts of 2,2'-oxybispropane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-bab01c9e180546239a0ffe7957edbf84
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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