1,1'-Thiocarbonyldi-2(1H)-pyridone → 6-Isothiocyanato-2,4-dimethylnicotinonitrile

HRID 1875947Notes

Reaction equation

HRID 1875947 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4]([CH3:11])[N:3]=1.[C:12](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:13]>ClCCl>[N:1]([C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4]([CH3:11])[N:3]=1)=[C:12]=[S:13]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 37932996-Amino-2,4-dimethyl-3-pyridinecarbonitrile

Product 1

HCID 183162016-Isothiocyanato-2,4-dimethylnicotinonitrileYield 790%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 6-amino-2,4-dimethylnicotinonitrile (0.14 g, 0.95 mmol) in dichloromethane (20 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.23 g, 0.1 mmol). The reaction was stirred at 40° C. for 3 hours. The reaction was cooled to room temperature. The crude was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane) to yield 6-isothiocyanato-2,4-dimethylnicotinonitrile (0.15 g, 0.79 mmol, 83% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 7.37 (s, 1H), 2.63 (s, 3H). MS (LC/MS) R.T.=2.40; [M+H]+=190.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe crude was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-848571a394bd470487c8310e9b1162ea
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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