Phosphorus oxychloride → 2-(Chloromethyl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazole

HRID 334518Notes

Reaction equation

HRID 334518 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.P(Cl)(Cl)(Cl)=O>C(#N)C>[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 24813Phosphorus oxychlorideHCID 674793863,4-dichloro-N'-(2-chloroacetyl)benzohydrazide

Product 1

HCID 27634662-(Chloromethyl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazoleYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3,4-dichlorobenzohydrazide 8 (0.5 mg, 2.43 mmol) and K2CO3 (0.61 g, 4.4 mmol) in acetonitrile (30 mL) was added 2-chloroacetyl chloride (0.41 g, 3.66 mmol) dropwise at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The solid was collected, Washed with H2O and ether, and dried to afford 3,4-dichloro-N′-(2-chloroacetyl)benzohydrazide 9 (0.59 g, 85%) which was used for the next step without further purification. A mixture of compound 9 (0.5.9 g, 2.24 mmol) and phosphorous oxychloride (0.51 g, 3.36 mmol) in acetonitrile (20 mL) was stirred under reflux for 16 hours and concentrated. The residue was subjected to flush column chromatography eluting with 10-25% acetone/hexanes to give compound 10 (0.43 g). Yield: 78%.

Workup

  1. customwas used for the next step without further purification
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated
  4. customto flush column chromatography
  5. washeluting with 10-25% acetone/hexanes

Sources & evidence

ORD record
ord-698e6c47b1b14be2a31ffc8cde13cc95
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

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