Ethanol → HCID 70511180, compound

HRID 1759324Notes

Reaction equation

HRID 1759324 reaction equation
[CH2:1]([N:8]1[C:12]([Cl:13])=[C:11]([CH2:14][C:15]#N)[N:10]=[C:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:31])=CC=1.[CH2:35]([OH:37])[CH3:36]>>[ClH:13].[CH2:1]([N:8]1[C:12]([Cl:13])=[C:11]([CH2:14][C:15]([O:37][CH2:35][CH3:36])=[O:31])[N:10]=[C:9]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 13022617HCID 13022617, compound

Product 1

HCID 70511180HCID 70511180, compound

Procedure

3.1 g of 1-benzyl-5-chloro-2-phenyl-4-cyanomethylimidazole, together with 2.1 g of p-toluenesulfonic acid monohydrate, was boiled in 100 ml of ethanol for 10 hours. The reaction solution was evaporated to dryness under reduced pressure, and the residue was dissolved in 50 ml of chloroform, followed by washing with 50 ml each of a 5% aqueous sodium bicarbonate solution and water to evaporate the chloroform layer to dryness under reduced pressure. The residue was chromatographed on a column of 60 g of silica gel, and eluted with chloroform. The fractions of the objective compound were collected and evaporated to dryness under reduced pressure, followed by dissolving the residue in 2 ml of 20% hydrogen chloride-ethanol. Upon addition of 50 ml of ether, there was obtained 1.5 g of ethyl 1-benzyl-5-chloro-2-phenylimidazole-4-acetate hydrochloride as colorless prisms, m.p. 120°-124° C.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml of chloroform
  3. washby washing with 50 ml each of a 5% aqueous sodium bicarbonate solution and water
  4. customto evaporate the chloroform layer to dryness under reduced pressure
  5. customThe residue was chromatographed on a column of 60 g of silica gel
  6. washeluted with chloroform
  7. customThe fractions of the objective compound were collected
  8. customevaporated to dryness under reduced pressure
  9. dissolutionby dissolving the residue in 2 ml of 20% hydrogen chloride-ethanol
  10. additionUpon addition of 50 ml of ether

Sources & evidence

ORD record
ord-0c772b1268934a9c9ce818f03b84e1cc
Source dataset
uspto-grants-1982_07
Patent number
US04340598

Reaction notes

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