Hydrogen Sulfide → 4-Methylpyridine-3-carbothioamide

HRID 1830862Notes

Reaction equation

HRID 1830862 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[SH2:17]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][N:5]=[CH:6][C:7]=1[C:8](=[S:17])[NH2:9]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 2278064-Methyl-3-cyanopyridine

Product 1

HCID 220497214-Methylpyridine-3-carbothioamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound (14)(9.2 g, 77.9 mmol) in dimethylformamide (500 ml) was added triethylamine (800 mg, 7.79 mmol; 10 mol %), and the mixture was stirred at room temperature for 16 hrs. while introducing hydrogen sulfide gas. The solvent was concentrated and the obtained residue was partitioned between dichloromethane and brine. The aqueous layer was extracted with dichloromethane. The extracts were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from a small amount of ethyl acetate to give the title compound (10.2 g, 86%).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe obtained residue was partitioned between dichloromethane and brine
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was recrystallized from a small amount of ethyl acetate

Sources & evidence

ORD record
ord-117a81a9be09494c8390edd7c9033d4f
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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