4-Chlorobenzoyl chloride → 3-(Chloromethyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole

HRID 1276198Notes

Reaction equation

HRID 1276198 reaction equation
[Cl:1][CH2:2][C:3](=[N:5][OH:6])[NH2:4].C(=O)(O)[O-].[Na+].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=O)=[CH:15][CH:14]=1>CC(C)=O>[Cl:1][CH2:2][C:3]1[N:4]=[C:17]([C:16]2[CH:20]=[CH:21][C:13]([Cl:12])=[CH:14][CH:15]=2)[O:6][N:5]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 41122522-chloro-N'-hydroxyethanimidamide

Product 1

HCID 125699523-(Chloromethyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-chloroacetamidoxime (0.5 g) and sodium bicarbonate (0.78 g) in 10 mL of anhydrous acetone was treated with 4-chlorobenzoyl chloride (0.58 mL) at room temperature for 2 hours, concentrated in vacuo, dissolved in water and extracted with ethyl acetate. The organic layers were combined, dried with MgSO4 and concentrated to a semi-solid. This material was redissolved in toluene (50 mL). refluxed under nitrogen for 15 hours, cooled and absorbed on to silica gel. Chromatography using ethyl acetate:hexane (1:9) gave the pure title product as a light yellow solid, mp 79-80° C. Mass spectrum m/e: 228 (M+), 1H NMR (250 MHz, CDCl3) δ 8.1 (d, 2H), 7.5 (d, 2H), 4.7 (s, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated to a semi-solid
  6. dissolutionThis material was redissolved in toluene (50 mL)
  7. temperaturerefluxed under nitrogen for 15 hours
  8. temperaturecooled
  9. customabsorbed on to silica gel

Sources & evidence

ORD record
ord-8ce304b8faea4ed0b77422013a8ec725
Source dataset
uspto-grants-2000_12
Patent number
US06166020

Reaction notes

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