Chloroacetyl chloride → 5-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole

HRID 1276197Notes

Reaction equation

HRID 1276197 reaction equation
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][CH2:19][C:20](Cl)=O>C1(C)C=CC=CC=1>[Cl:18][CH2:19][C:20]1[O:10][N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 69186N'-Hydroxybenzenecarboximidamide

Product 1

HCID 9667145-(Chloromethyl)-3-phenyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of benzamidoxime (0.77 g, 5.68 mmol) and triethylamine (0.95 mL, 0.82 mmol) in toluene (10 mL) was treated with 0.45 mL (5.65 mmol) of chloroacetyl chloride at room temperature for 30 min., refluxed for 18 hours, cooled to room temperature and concentrated in vacuo. The residue was diluted with water, and extracted with ethyl acetate. The organic extracts were then washed with water and dried with MgSO4. Concentration in vacuo gave an oil which was chromatographed on silica gel using ethyl acetate, hexanes (1.9), giving 0.24 of the title compound as a light yellow oil which solidified on standing. 1H NMR (250 MHz, CDCl3) δ 8.1 (m, 2H), 7.5 (m, 3H), 4.8 (s, 2H).

Workup

  1. temperaturerefluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were then washed with water
  6. dry with materialdried with MgSO4
  7. concentrationConcentration in vacuo
  8. customgave an oil which
  9. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-4e0053c1124544af94da13468bf40ef5
Source dataset
uspto-grants-2000_12
Patent number
US06166020

Reaction notes

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