1,1'-Thiocarbonyldi-2(1H)-pyridone → 1-(4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

HRID 1803125Notes

Reaction equation

HRID 1803125 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1)[NH2:6].[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[N:6]([C:5]1[CH:7]=[CH:8][C:9]([N:10]2[CH:14]=[N:13][C:12]([CH3:15])=[N:11]2)=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:16]=[S:17]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

Product 1

HCID 866498971-(4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step F (3): Dichloromethane (125 mL) was added to a flask charged with 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (4.00 g, 19.59 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (4.55 g, 19.59 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 1-(4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (3.91 g, 15.88 mmol, 81% yield) as a white solid. LC-MS (M+H)+ 247.0. 1H NMR (500 MHz, chloroform-d) δ ppm 8.64 (s, 1 H) 7.78 (d, J=8.55 Hz, 1 H) 6.96 (dd, J=8.55, 2.14 Hz, 1 H) 6.90 (d, J=2.14 Hz, 1 H) 3.94 (s, 3 H) 2.48 (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-6a4ab9412ee148ebad50642e2ca2d4ed
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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