Imidazole → HCID 14991021, compound

HRID 2166055Notes

Reaction equation

HRID 2166055 reaction equation
Cl[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH2:21][C:22]([CH3:25])([CH3:24])[N:23]=2)=[CH:15][CH:14]=1)[C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[N:9][N:8]([CH3:11])[C:7]=2[CH:12]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>C(#N)C>[CH3:24][C:22]1([CH3:25])[CH2:21][O:20][C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:2]([N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[C:3]3[CH:4]=[CH:5][C:6]4[N:10]=[N:9][N:8]([CH3:11])[C:7]=4[CH:12]=3)=[CH:14][CH:15]=2)=[N:23]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 19995896HCID 19995896, compound

Product 1

HCID 14991021HCID 14991021, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 10 parts of 6-[chloro[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]methyl]-1-methyl-1H-benzotriazole and 10 parts of 1H-imidazole in 80 parts of acetonitrile was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated and the product was extracted with ethyl acetate. The extract was washed with a diluted potassium carbonate solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 7.1 parts (65.6%) of 6-[[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl](1H-imidazol-1-yl)methyl]-1-methyl-1H-benzotriazole as a residue (int. 231).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with a diluted potassium carbonate solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-94d942f315ac4bae91fbe452aa52a5b7
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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