Imidazole → HCID 14518519, compound

HRID 1723133Notes

Reaction equation

HRID 1723133 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8](=[O:10])[NH:9][C:5]=2[CH:4]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>CN(C)C=O>[N:13]1([CH2:2][C:3]2[CH:12]=[CH:11][C:6]3[NH:7][C:8](=[O:10])[NH:9][C:5]=3[CH:4]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 20026586HCID 20026586, compound

Product 1

HCID 14518519HCID 14518519, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6.35 parts of 5-(chloromethyl)-1,3-dihydro-2H-benzimidazol-2-one, 11.9 parts of 1H-imidazole and 135 parts of N,N-dimethylformamide was stirred overnight at 80° C. The whole was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (80:20 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. After standing over weekend at room temperature, the residue was solidified. The product was pulverized and stirred in acetonitrile. The product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (87:13 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was dried in a dry-pistol at 130° C., yielding 0.75 parts (10%) of 1,3-dihydro-5-(1H-imidazol-1-ylmethyl)-2H-benzimidazol-2-one; mp. 254.5° C. (compound 24).

Workup

  1. customThe whole was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (80:20 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. waitAfter standing over weekend at room temperature
  7. stirringstirred in acetonitrile
  8. filtrationThe product was filtered off
  9. custompurified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (87:13 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was dried in
  14. customa dry-pistol at 130° C.

Sources & evidence

ORD record
ord-ecaba034f32443b8a6992c35a2d3f190
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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