Sulfuric Acid → HCID 14305256, compound

HRID 622312Notes

Reaction equation

HRID 622312 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH:27]1(O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:8]2[C:12]([C:13]([O:15][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:14])=[CH:11][N:10]=[CH:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7966CyclohexanolHCID 14305254HCID 14305254, compound

Product 1

HCID 14305256HCID 14305256, compoundYield 28.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 7 parts of 1-[phenyl(2-pyridinyl)methyl]-1H-imidazole-5-carboxylic acid, 5.5 parts of concentrated sulfuric acid and 140 parts of cyclohexanol was stirred for 2 days at 100° C. The reaction mixture was evaporated (at an oil pump) and the residue was taken up in dichloromethane. The organic layer was washed with a sodium hydroxide solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried in vacuo at 60° C., yielding 2.6 parts (28.8%) of cyclohexyl 1-[phenyl(2-pyridinyl)methyl]-1H-imidazole-5-carboxylate; mp. 161.0° C. (compound 1.255).

Workup

  1. customThe reaction mixture was evaporated (at an oil pump) and the residue
  2. washThe organic layer was washed with a sodium hydroxide solution
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile
  11. filtrationThe product was filtered off
  12. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-35bc88c801724dcebcdce623da0507d3
Source dataset
uspto-grants-1988_09
Patent number
US04770689

Reaction notes

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