Toluene → 3-Benzyl-5-(chloromethyl)-1,2,4-oxadiazole

HRID 1076351

Reaction equation

HRID 1076351 reaction equation
[C:1]1([CH2:7][C:8](=[N:10][OH:11])[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[Cl:19][CH2:20][C:21](OC(=O)CCl)=O>O>[CH2:7]([C:8]1[N:9]=[C:21]([CH2:20][Cl:19])[O:11][N:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 10946Chloroacetic anhydrideHCID 2731007N'-hydroxy-2-phenylethanimidamide

Product 1

HCID 80271323-Benzyl-5-(chloromethyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 40 g. (0.27 mole) of crude phenylacetamide oxime in 200 ml. of dry toluene is treated with 45.9 g. (0.27 mole) of chloroacetic anhydride in 100 ml. of toluene. The resultant mixture is then refluxed and the water formed is removed by means of a Dean Stark trap. The mixture is refluxed for 3-4 hours after which it is cooled and extracted once with 150 ml. of water and four times with 100 ml. of a saturated sodium bicarbonate solution. The toluene solution is then dried over magnesium sulfate and the solvent is removed in vacuo. Upon distillation of the residue, 3-benzyl-5-chloromethyl-1,2,4-oxadiazole, 19.8 g. having a b.p. of 100-108 (0.04 mm) is obtained.

Workup

  1. customis removed by means of a Dean Stark trap
  2. temperatureThe mixture is refluxed for 3-4 hours after which it
  3. temperatureis cooled
  4. extractionextracted once with 150 ml
  5. dry with materialThe toluene solution is then dried over magnesium sulfate
  6. customthe solvent is removed in vacuo
  7. distillationUpon distillation of the residue, 3-benzyl-5-chloromethyl-1,2,4-oxadiazole, 19.8 g
  8. customof 100-108 (0.04 mm) is obtained

Sources & evidence

ORD record
ord-483001fa9ecb4ec4a5cf82aadac32f15
Source dataset
uspto-grants-1976_05
Patent number
US03956498

Linked notes

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