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

HRID 1076352Notes

Reaction equation

HRID 1076352 reaction equation
[Cl:1][CH2:2][C:3](=[N:5][OH:6])[NH2:4].Cl.[C:8]1(N=CC(OCC)=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:21](O)[CH3:22]>>[Cl:1][CH2:2][C:3]1[N:4]=[C:21]([CH2:22][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:6][N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 41122522-chloro-N'-hydroxyethanimidamideHCID 21540475Ethyl phenyliminoacetate hydrochloride

Product 1

HCID 120442135-Benzyl-3-(chloromethyl)-1,2,4-oxadiazole

Procedure

A mixture of chloroacetamide oxime, 11.0 g. (0.10 mole), and ethyl phenyliminoacetate hydrochloride, 22 g. (0.11 mole), in 80 ml. of absolute ethanol is refluxed for one hour. After cooling, the ammonium chloride which precipitates is filtered off and the alcohol is removed in vacuo. Upon steam distillation of the residue, 7.0 gm. of 3-chloromethyl-5-benzyl-1,2,4-oxadiazole is obtained, n20 1.5386.

Workup

  1. temperatureAfter cooling
  2. customthe ammonium chloride which precipitates
  3. filtrationis filtered off
  4. customthe alcohol is removed in vacuo
  5. distillationUpon steam distillation of the residue, 7.0 gm

Sources & evidence

ORD record
ord-c563bab3674c40f2bb308f1a8f37b253
Source dataset
uspto-grants-1976_05
Patent number
US03956498

Reaction notes

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