m-Chloroperbenzoic acid → 6-Amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-one

HRID 2291225Notes

Reaction equation

HRID 2291225 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][N:7]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8]([CH3:9])=[O:20])=[N:6][N:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 115428516-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 198565676-Amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-oneYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.7 g of 6-amino-4-methyl-3-methylthio-1,2,4-triazin-5-one are dispersed in 200 ml of methylene chloride, and 1.8 g of 3-chloroperbenzoic acid are added in portions at 15°-20° C. A clear yellow solution is thereby formed and is evaporated at 40° C. in vacuo. The solid residue is treated with ethyl acetate, whereupon the 3-chlorobenzoic acid formed in the reaction dissolves completely. The undissolved pure product is filtered off to give 1.1 g of 6-amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-one with a melting point of 189° C. (decomposition).

Workup

  1. customA clear yellow solution is thereby formed
  2. customis evaporated at 40° C. in vacuo
  3. additionThe solid residue is treated with ethyl acetate, whereupon the 3-chlorobenzoic acid
  4. customformed in the reaction
  5. dissolutiondissolves completely
  6. filtrationThe undissolved pure product is filtered off

Sources & evidence

ORD record
ord-b7b3559d4ae643588b3a09da6bd74d09
Source dataset
uspto-grants-1989_01
Patent number
US04795486

Reaction notes

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