Imidazole → HCID 19816069, compound

HRID 2247912Notes

Reaction equation

HRID 2247912 reaction equation
Cl[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[NH:7][CH2:6]2.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.C(#N)C>CS(C)=O>[N:20]1([CH:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[NH:7][CH2:6]3)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6342AcetonitrileHCID 54554301HCID 54554301, compound

Product 1

HCID 19816069HCID 19816069, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3.6 parts of 6-(chlorophenylmethyl)-3,4-dihydro-2(1H)-quinazolinone, 5.3 parts of 1H-imidazole, 60 parts of acetonitrile and 27.5 parts of dimethyl sulfoxide was stirred for 4 hours at reflux temperature. After concentration, the residue was washed twice with water, dissolved in a mixture of trichloromethane and methanol (90:10 by volume), dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a 45 parts of ethyl acetate and a few drops of water. The product was filtered off, washed with ethyl acetate and 2,2'-oxybispropane and dried, yielding 2.3 parts (58.1%) of 3,4-dihydro-6-[(1H-imidazol-1-yl)phenylmethyl]-2(1H)-quinazolinone; mp. 222.5° C. (comp. 16).

Workup

  1. temperatureat reflux temperature
  2. concentrationAfter concentration
  3. washthe residue was washed twice with water
  4. dissolutiondissolved in a mixture of trichloromethane and methanol (90:10 by volume)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from a 45 parts of ethyl acetate and a few drops of water
  13. filtrationThe product was filtered off
  14. washwashed with ethyl acetate and 2,2'-oxybispropane
  15. customdried

Sources & evidence

ORD record
ord-7ec79e951b454546846a545c3bef5205
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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