1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-Isothiocyanato-5-(methylthio)pyrazine

HRID 250083Notes

Reaction equation

HRID 250083 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][S:18][C:19]1[N:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=1>ClCCl>[N:25]([C:22]1[CH:21]=[N:20][C:19]([S:18][CH3:17])=[CH:24][N:23]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 218972225-(Methylthio)pyrazin-2-amine

Product 1

HCID 574765802-Isothiocyanato-5-(methylthio)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (1.069 g, 4.60 mmol) in dichloromethane at room temperature was added 5-(methylthio)pyrazin-2-amine (0.50 g, 3.54 mmol). The reaction was stirred at room temperature for 18 hours. LC/MS showed the desired product peak as the major peak. The deep orange mixture was purified by silica gel chromatography (0-40% ethyl acetate-hexanes) to afford 2-isothiocyanato-5-(methylthio)pyrazine (0.545 g, 0.257 mmol, 84% yield) as an orange oil. LCMS R.T.=2.65; [M+H]+=184.02.

Sources & evidence

ORD record
ord-2b86771e4ac4470797aeb0713df67088
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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