Ethanol → HCID 66759550, compound

HRID 1402774Notes

Reaction equation

HRID 1402774 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14].[CH2:24](O)[CH3:25]>Cl>[N:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:9]=1[CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([O:15][CH2:24][CH3:25])=[O:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 66759374HCID 66759374, compound

Product 1

HCID 66759550HCID 66759550, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(2-Aminophenyl)-3-(4-chlorophenyl)glutaramic acid (2.04 g) is dissolved in a mixture of ethanol (20 ml) and conc. HCl (5 ml) and heated to reflux overnight. The ethanol is removed in vacuo and the aqueous layer is neutralised with 10M NaOH. Saturated sodium bicarbonate solution (40 ml) is added and the aqueous layer is extracted twice with dichloromethane (50 ml). The combined organic layers are dried (sodium sulfate) and concentrated. The residue is purified by flash chromatography (dichloromethane/3% methanol/1% triethyl amine) on silica gel to afford ethyl 4-(2-benzimidazolyl)-3-(4-chlorophenyl)butanoate (1.39 g) as yellowish solid.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe ethanol is removed in vacuo
  4. additionSaturated sodium bicarbonate solution (40 ml) is added
  5. extractionthe aqueous layer is extracted twice with dichloromethane (50 ml)
  6. dry with materialThe combined organic layers are dried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (dichloromethane/3% methanol/1% triethyl amine) on silica gel

Sources & evidence

ORD record
ord-f5a902ea76ee4135bebc18ab70888583
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

Loading…