Methanol → HCID 22916391, compound

HRID 265357Notes

Reaction equation

HRID 265357 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:39]O>>[CH3:39][O:2][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10003259HCID 10003259, compound

Product 1

HCID 22916391HCID 22916391, compoundYield 54%

Procedure

A mixture of 1-(7-carboxyheptyl)-2,4,5-triphenyl-imidazole (0.5 g), concentrated sulphuric acid (2 ml) and methanol (100 ml) was heated at reflux for 24 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (50 ml), washed with water (50 ml), saturated NaHCO3 solution (50 ml), water (50 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chromatography on silica gel eluted with a dichloromethane:methanol gradient gave 1-(7-methoxycarbonylheptyl)-2,4,5-triphenylimidazole (0.28 g, 54%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  5. washwashed with water (50 ml), saturated NaHCO3 solution (50 ml), water (50 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to dryness in vacuo
  8. washColumn chromatography on silica gel eluted with a dichloromethane

Sources & evidence

ORD record
ord-697197b9f7214b9da5af245d73385da1
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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