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

HRID 1875945Notes

Reaction equation

HRID 1875945 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1.[C:11](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:12]>ClCCl>[N:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1)=[C:11]=[S:12]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 27946626-Amino-2-methylpyridine-3-carbonitrile

Product 1

HCID 574765786-Isothiocyanato-2-methylnicotinonitrileYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 6-amino-2-methylnicotinonitrile (0.41 g, 3.08 mmol) in dichloromethane (20 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.75 g, 3.23 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-methylnicotinonitrile (0.52 g, 2.97 mmol, 96% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 8.36 (d, J=8.24 Hz, 1H), 7.39 (d, J=8.24 Hz, 1H), 2.65 (s, 3H). MS (LC/MS) R.T.=2.09; [M+H]+=176.0.

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-26513b0c422e4a8aa60a53cd3ca1978a
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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