Methane → Dazoxiben hydrochloride

HRID 1462929Notes

Reaction equation

HRID 1462929 reaction equation
[I-].C([N+:5]1[CH:9]=[CH:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=2)[CH:6]=1)(=O)C.[ClH:24].C>>[ClH:24].[N:7]1([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)[CH:8]=[CH:9][N:5]=[CH:6]1

Participants

4

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 178469086HCID 178469086, compound

Product 1

HCID 53000Dazoxiben hydrochlorideYield 79%

Conditions

Temperature
80 °C

Procedure

A mixture of 1.3 g of 1-acetyl-3-[2-(4-ethoxycarbonylphenoxy)ethyl]imidazolium iodide in 100 ml of 2N-hydrochloric acid was heated at 80° C. for 2 hours. After cooling, the solution was treated with an activated charcoal and concentrated under reduced pressure. The residue were triturated with acetone and the resulting crystals were filtered and dried to obtain 0.64 g of 4-[2-(1-imidazolyl)ethoxy]benzoic acid hydrochloride (79.0% yield). Colorless granules.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated under reduced pressure
  3. customThe residue were triturated with acetone
  4. filtrationthe resulting crystals were filtered
  5. customdried

Sources & evidence

ORD record
ord-5689bed42282430796536df83ba3995b
Source dataset
uspto-grants-1984_07
Patent number
US04461905

Reaction notes

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