Methanol → HCID 13075869, compound

HRID 223507Notes

Reaction equation

HRID 223507 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH3:30]O>>[Cl:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:6]=1[CH2:7][C:8]([O:10][CH3:30])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12822124HCID 12822124, compound

Product 1

HCID 13075869HCID 13075869, compound

Procedure

In 100 ml of methanol was dissolved 1.8 g of 4-chloro-1-(4-methylbenzyl)-2-phenylimidazole-5-acetic acid, and 0.5 ml of concentrated sulfuric acid was added to the solution to boil for 2 hours. The reaction solution was evaporated to dryness under reduced pressure, and 50 ml each of ethyl acetate and a 10% aqueous sodium bicarbonate solution were added to the residue to shake. The ethyl acetate layer, after washing with water, was evaporated to dryness under reduced pressure. The residue was dissolved in a small amount of methanol and there was obtained, upon standing, 1.5 g of methyl 4-chloro-1-(4-methylbenzyl)-2-phenylimidazole-5-acetate as colorless, prism-formed crystals, m.p. 92°-95° C.

Workup

  1. additionwas added to the solution
  2. customThe reaction solution was evaporated to dryness under reduced pressure, and 50 ml each of ethyl acetate
  3. additiona 10% aqueous sodium bicarbonate solution were added to the residue
  4. washThe ethyl acetate layer, after washing with water
  5. customwas evaporated to dryness under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of methanol
  7. customthere was obtained

Sources & evidence

ORD record
ord-85434cdc7b534edebbe3c8e2c32f7d91
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

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