Benzenesulfinic acid, sodium salt → Methyl 6-methyl-3-nitro-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetate

HRID 1069445Notes

Reaction equation

HRID 1069445 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:13])[C:5]([N+:14]([O-:16])=[O:15])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[C:25]1([S:31]([O-:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Na+]>O1CCCC1>[CH3:1][C:2]1[N:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:13])[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[CH:3]=1

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 11079278Methyl 6-methyl-3-nitro-2-oxo-4-[[(trifluoromethyl)sulphonyl]oxy]-1,2-dihydropyridine-1-acetate

Product 1

HCID 86757070Methyl 6-methyl-3-nitro-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.24 g (14 mmol) of methyl 6-methyl-3-nitro-2-oxo-4-[[(trifluoromethyl)sulphonyl]oxy]-1,2-dihydropyridine-1-acetate in solution in 50 ml of tetrahydrofuran are added dropwise to 2.38 g (14.5 mmol) of sodium benzenesulphinate in suspension in 100 ml of tetrahydrofuran and the mixture is left for 3 hours at room temperature. The solvent is evaporated off, the residue is taken up in 200 ml of dichloromethane and washed with 50 ml of a 1 N aqueous hydrochloric acid solution. The organic phase is recovered, it is dried over magnesium sulphate and evaporated off.

Workup

  1. customThe solvent is evaporated off
  2. washwashed with 50 ml of a 1 N aqueous hydrochloric acid solution
  3. customThe organic phase is recovered
  4. dry with materialit is dried over magnesium sulphate
  5. customevaporated off

Sources & evidence

ORD record
ord-cea63d14dfda4c14a938a155153441b4
Source dataset
uspto-grants-2001_06
Patent number
US06252082B1

Reaction notes

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