Ammonia → HCID 23499173, compound

HRID 361404Notes

Reaction equation

HRID 361404 reaction equation
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[S:15]1[CH2:20]CC(=O)[CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:17][CH2:16][S:15][CH2:20][C:4]=2[CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 66173Tetrahydrothiopyran-4-oneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 23499173HCID 23499173, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-3,5-dinitro-2-pyridone (0.6 g, 3.0 mmol), tetrahydrothiopyran-4-one (0.35 g, 3.0 mmol) and ammonia solution in methanol (2.0M, 30 mL) was refluxed for 6 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portico was flash chromatographed over silica pel (eluent: 90:1 v/v ethyl acetate-hexane) to give a yellow solid (0.586 g, 99% yield).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customchromatographed over silica pel (eluent: 90:1 v/v ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d5ad1a2ac9944d6196c98db657c67cc1
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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