Acetic Acid → 3-(2,3-Dichloro-phenylsulphonylmethyl)-5-methyl-1,2,4-oxadiazole

HRID 22297

Reaction equation

HRID 22297 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:10][C:11]1[N:15]=[C:14]([CH3:16])[O:13][N:12]=1.C(O)(=[O:19])C.OO.[OH2:23]>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([CH2:10][C:11]1[N:15]=[C:14]([CH3:16])[O:13][N:12]=1)(=[O:19])=[O:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 199286583-(2,3-Dichlorophenylthiomethyl)-5-methyl-1,2,4-oxadiazole

Product 1

HCID 199286533-(2,3-Dichloro-phenylsulphonylmethyl)-5-methyl-1,2,4-oxadiazoleYield 38.9%

Procedure

3.9 g (14.2 mmol) of 3-(2,3-dichloro-phenylthiomethyl)-5-methyl-1,2,4-oxadiazole are introduced into 50 ml of glacial acetic acid and the mixture is treated with 9.8 ml of 30% strength hydrogen peroxide. The mixture is stirred at reflux temperature until the reaction is complete (approximately 2 hours). The entire batch is then introduced into 200 ml of water, and the crude product which has precipitated is separated off and recrystallised from isopropanol. 1.7 g (38.9% of theory) of 3-(2,3-dichloro-phenylsulphonylmethyl)-5-methyl-1,2,4-oxadiazole are obtained.

Workup

  1. temperatureat reflux temperature until the reaction
  2. custom(approximately 2 hours)
  3. customthe crude product which has precipitated
  4. customis separated off
  5. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-7283eb6303524a3a9e352018e96f932b
Source dataset
uspto-grants-1995_06
Patent number
US05428047

Linked notes

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