Sodium Thiosulfate → HCID 57815209, compound

HRID 385538Notes

Reaction equation

HRID 385538 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.ClC1C=CC=C(C(OO)=[O:20])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][CH:8]=[N+:9]([O-:20])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 128788183-Bromo-1,5-naphthyridine

Product 1

HCID 57815209HCID 57815209, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 50 mL of chloroform, 5.00 g of 3-bromo-1,5-naphthyridin was dissolved, 6.40 g of m-chloroperbenzoic acid was added thereto, and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, a 5% aqueous sodium thiosulfate solution and chloroform were added, and the organic layer was separated, washed sequentially with a 5% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of ethyl acetate:hexane=1:1 to obtain 1.95 g of 3-bromo-1,5-naphthyridin-5-oxide as a light yellow solid.

Workup

  1. customthe organic layer was separated
  2. washwashed sequentially with a 5% aqueous sodium hydroxide solution
  3. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-480df686cd62472b844e692a63074c52
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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