6-Bromo-4-nitropyridine-2-carboxamide → 6-Bromo-4-(4-nitrophenylsulphanyl)-pyridine-2-carboxamide

HRID 1603629Notes

Reaction equation

HRID 1603629 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[K].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[C:4]([S:24][C:21]2[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 196055336-Bromo-4-nitropyridine-2-carboxamideHCID 700026814Nitrothiophenol potassium salt

Product 1

HCID 196054946-Bromo-4-(4-nitrophenylsulphanyl)-pyridine-2-carboxamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.25 g (0.001 mol) of 6-bromo-4-nitropyridine-2-carboxamide was dissolved in 5 ml of dimethylformamide, treated with 0.19 g (0.001 mol) of 4-nitrothiophenol potassium salt and stirred at room temperature for 18 hrs. The reaction mixture was partitioned in water and ethyl acetate and the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4 and concentrated in a vaccum. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There was obtained 0.31 g (86%) of 6-bromo-4-(4-nitrophenylsulphanyl)-pyridine-2-carboxamide as yellowish crystals; m.p.: 192-194° C. (dec.).

Workup

  1. customThe reaction mixture was partitioned in water
  2. washethyl acetate and the organic phase was washed with water and sat. sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in a vaccum
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-76fa1f9c95374dc0bcaa645581d33804
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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