m-Chloroperbenzoic acid → 3,4-Dimethoxy-1,2,5-thiadiazole 1-oxide

HRID 2418022Notes

Reaction equation

HRID 2418022 reaction equation
[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[N:6][S:5][N:4]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[N:6][S:5](=[O:18])[N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 122294673,4-Dimethoxy-1,2,5-thiadiazole2×

Product 1

HCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 3,4-dimethoxy-1,2,5-thiadiazole (35.2 g; 24.1 mmoles) [prepared according to the procedure described in J. Org. Chem., 40, 2749 (1975)] in 100 ml of chloroform was added over a period of 3 minutes to a stirred solution of m-chloroperbenzoic acid (50.7 g; 25.0 mmoles; 85% assay) in 900 ml of chloroform at 20°, using a cooling bath to keep the exothermic reaction from rising above 32°. After stirring for 3 hours at ambient temperature, the excess peracid was reacted with an additional 2.0 g of 3,4-dimethoxy-1,2,5-thiadiazole and stirred for 1 hour.

Workup

  1. customthe exothermic reaction
  2. customfrom rising above 32°
  3. stirringstirred for 1 hour

Sources & evidence

ORD record
ord-689f7bc25bc847439d307c749baeb940
Source dataset
uspto-grants-1984_09
Patent number
US04471122

Reaction notes

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