Ethanol → HCID 178469892, compound

HRID 250811Notes

Reaction equation

HRID 250811 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11]O)=[NH:10])=[CH:4][CH:3]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].CCO.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:18]([O:17][C:13]([C:14]1[N:10]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[NH:11][CH:15]=1)=[O:16])[CH3:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 7583Diphenyl EtherHCID 12182Ethyl propiolateHCID 178510745HCID 178510745, compound

Product 1

HCID 178469892HCID 178469892, compoundYield 49%

Conditions

Temperature
190 °C

Procedure

2-(4-bromophenyl)-N-hydroxyacetamidine (5.0 g, 21.8 mmol) and ethyl propiolate (2.4 mL, 24.0 mmol) were dissolved in EtOH (100 mL, 2 mol). The mixture was heated to reflux for 7 hours, cooled and then concentrated. The residue was then dissolved in diphenyl ether (75 mL, 470 mmol), heated at 190° C. for 2 hours, cooled, combined with 400 mL of hexanes, and allowed to sit overnight. The solvent was decanted and the precipitant was dissolved in DCM and purified by column chromatography (0-10% MeOH in DCM) to yield 2-(4-bromobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (3.3 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 7 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. temperaturecooled
  6. customThe solvent was decanted
  7. dissolutionthe precipitant was dissolved in DCM
  8. custompurified by column chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-3aff55e01e8943c4ba523825670e5527
Source dataset
uspto-grants-2011_01
Patent number
US07863309B2

Reaction notes

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