HCID 19081376, compound → HCID 19081389, compound

HRID 963198Notes

Reaction equation

HRID 963198 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9](Cl)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][SH:17].[Na]>O1CCOCC1>[C:1]([N:5]1[C:10](=[O:11])[C:9]([S:17][CH3:16])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19081376HCID 19081376, compoundHCID 45051789Methylmercaptan sodium

Product 1

HCID 19081389HCID 19081389, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into 20 ml of a dioxane solution of 2.31 g of 2-tert-butyl-4-chloro-5-nitropyridazin-3-(2H)-one, 5 ml of an aqueous solution of 0.7 g of sodium methylmercaptan was dropwise added over a period of 4 minutes under cooling with ice. The mixture was stirred at room temperature for 10 minutes and then extracted with ethyl acetate. The extract was washed with water and then with saturated sodium chloride aqueous solution, and then it was dried over anhydrous sodium sulfate and concentrated. The residual oil was subjected to column chromatography, and using an eluent (n-hexane:ethyl acetate=20:1), 1.5 g of oily 2-tert-butyl-4-methylthio-5-nitropyridazin-3-(2H)-one was obtained.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialwith saturated sodium chloride aqueous solution, and then it was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca96e41f5b784441af458da0c2a5f5a0
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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