Thionyl Chloride → HCID 57808403, compound

HRID 2105179Notes

Reaction equation

HRID 2105179 reaction equation
[CH2:1]([C:8]1[CH:26]=[CH:25][CH:24]=[CH:23][C:9]=1[C:10]([NH:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl>C1C=CC=CC=1>[CH2:1]([C:8]1[CH:26]=[CH:25][CH:24]=[CH:23][C:9]=1[C:10]1[O:22][C:14]([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 44594095HCID 44594095, compound

Product 1

HCID 57808403HCID 57808403, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 19 (1.1 g, 3.194 mmol) in 4 mL benzene was added SOCl2 (2.2 mL, 30.13 mmol). The mixture was heated to reflux overnight and then solvent and excess SOCl2 were evaporated. The yellow residue was dissolved in EtOAc. The organic layer was washed with saturated NaHCO3 aqueous solution, H2O and brine, dried over MgSO4 and concentrated. The crude product was purified by flash column chromatography (8-10% EtOAc in n-hexane) to give 2-(2-benzyl-phenyl)-5-m-tolyl-[1,3,4]-oxadiazole 21 (1.0 g, 3.064 mmol, 96% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customsolvent and excess SOCl2 were evaporated
  4. dissolutionThe yellow residue was dissolved in EtOAc
  5. washThe organic layer was washed with saturated NaHCO3 aqueous solution, H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (8-10% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-1e62bb510e134b1683497f9b9cd1dc2e
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

Loading…