1,1'-Thiocarbonyldi-2(1H)-pyridone → 5-isothiocyanato-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1803130Notes

Reaction equation

HRID 1803130 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][C:12]([CH3:15])=[N:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][C:12]([CH3:15])=[N:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8])=[C:16]=[S:17]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 668600535-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

Product 1

HCID 866498995-isothiocyanato-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step G (3): Dichloromethane (100 mL) was added to a flask charged with 5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile (6.59 g, 33.1 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (7.68 g, 33.1 mmol). The resulting mixture was stirred for 24 h at rt. The crude reaction mixture was concentrated and the crude products were purified using silica gel chromatography (0-5% EtOAc/chloroform) linear gradient to afford 5-isothiocyanato-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile (5.19 g, 15.88 mmol, 56% yield) as a yellow solid. LC-MS (M+H)+ 242.0.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe crude products were purified

Sources & evidence

ORD record
ord-7aff804e3ac4437d9b6f92c817bb14e4
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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