Potassium Carbonate → O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate

HRID 1731289

Reaction equation

HRID 1731289 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[O:26][C:27](Cl)=[S:28]>CC(C)=O>[CH3:9][N:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[C:27](=[S:28])[O:26][C:17]1[CH:18]=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 82681O-2-Naphthyl chlorothioformateHCID 3839092N,6-dimethylpyridin-2-amine

Product 1

HCID 13387378O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamateYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 1.22 g of 6-methyl-2-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise 2.23 g of 2-naphthylchlorothioformate in 20 ml of acetone under agitation at room temperature. The reaction mixture was stirred overnight at room temperature and inorganic salts were removed by filtration. After acetone was removed by distillation under a reduced pressure, the residue was purified by the column chromatography (silica gel, developed with ethyl acetate/benzene=1/9 (V/V), to obtain 2.62 g of O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate as a solid in a yield of 85%. A portion of the product was recrystallized from ethanol to give colorless crystals having a melting point of 149.5° C.-150.5° C. Elemental analysis of the crystals is given below.

Workup

  1. custominorganic salts were removed by filtration
  2. customAfter acetone was removed by distillation under a reduced pressure
  3. customthe residue was purified by the column chromatography (silica gel

Sources & evidence

ORD record
ord-7c37c20bfd6a4903b34100695eea24c5
Source dataset
uspto-grants-1986_11
Patent number
US04621090

Linked notes

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