Potassium Carbonate → 2-(Chloromethyl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazole

HRID 334523Notes

Reaction equation

HRID 334523 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[C:5]([NH:7][NH:8][C:9](=[O:12])[CH2:10][Cl:11])=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:11][CH2:10][C:9]1[O:12][C:5]([C:4]2[CH:13]=[CH:14][C:15]([Cl:16])=[C:2]([Cl:1])[CH:3]=2)=[N:7][N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 674793863,4-dichloro-N'-(2-chloroacetyl)benzohydrazide

Product 1

HCID 27634662-(Chloromethyl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazoleYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 9 (120 mg, 0.263 mmol), compound A (76 mg, 0.263 mmol) and K2CO3 (72.58 mg, 0.526 mmol) was heated under reflux in 25 ml of acetone for 3 hours. The reaction mixture was cooled to ambient temperature, filtered and the filtrate was evaporated to obtain crude residue which was purified by column chromatography using MeOH/DCM (15:85) as an eluent to obtain compound 10 as a yellow colored gummy material (75 mg). Yield: 40%.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customto obtain crude residue which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4e977790c0954e7b97e3a60e8940066d
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

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