HCID 14769542, compound → HCID 13577105, compound

HRID 2286985Notes

Reaction equation

HRID 2286985 reaction equation
[CH:1]([NH:3][C:4]1[S:8][N:7]=[C:6]([C:9](=[O:16])[CH:10](SC)[S:11]([CH3:13])=O)[N:5]=1)=[O:2].I([O-])(=O)(=O)=[O:18].[Na+]>C(O)(=O)C>[CH:1]([NH:3][C:4]1[S:8][N:7]=[C:6]([C:9](=[O:16])[C:10]([S:11][CH3:13])=[O:18])[N:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 14769542HCID 14769542, compoundHCID 23667635Sodium periodate

Product 1

HCID 13577105HCID 13577105, compoundYield 129.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-formamido-3-(2-methylthio-2-methylsulfinylacetyl)-1,2,4-thiadiazole (0.85 g) and sodium periodate (0.2 g) in glacial acetic acid (10 ml) was stirred for 45 minutes at 70° C. The reaction mixture was evaporated and the residue was dissolved in a mixture of ethyl acetate and water. The mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate and treated with an aqueous solution of sodium thiosulfate. The organic layer was separated, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with a mixture of diethyl ether and petroleum ether to give the title compound (280 mg), mp. 186° to 187° C.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. additiontreated with an aqueous solution of sodium thiosulfate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was triturated with a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-aba3668200d548f585189b113c163534
Source dataset
uspto-grants-1981_05
Patent number
US04268509

Reaction notes

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