1,1'-Thiocarbonyldi-2(1H)-pyridone → 1-(2-fluoro-4-isothiocyanatophenyl)-5-methyl-1H-1,2,4-triazole

HRID 1803111Notes

Reaction equation

HRID 1803111 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[C:13]([CH3:14])=[N:12][CH:11]=[N:10]1)[NH2:5].[C:15](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:16]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:5]=[C:15]=[S:16])[CH:6]=[CH:7][C:8]=1[N:9]1[C:13]([CH3:14])=[N:12][CH:11]=[N:10]1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 584144593-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)aniline

Product 1

HCID 866498911-(2-fluoro-4-isothiocyanatophenyl)-5-methyl-1H-1,2,4-triazoleYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step C (3): Dichloromethane (125 mL) was added to a flask charged with 3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)aniline (3.14 g, 16.3 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (3.79 g, 16.3 mmol). The resulting mixture was stirred for 24 h at rt and concentrated in vacuo. The crude residue was purified using silica gel chromatography (0-5% EtOAc/chloroform, linear gradient) to afford 1-(2-fluoro-4-isothiocyanatophenyl)-5-methyl-1H-1,2,4-triazole (3.18 g, 13.6 mmol, 83% yield) as a white solid. LC-MS (M+H)+ 235.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.99 (s, 1 H) 7.47 (t, J=8.24 Hz, 1 H) 7.13-7.22 (m, 2 H) 2.43 (d, J=1.83 Hz, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was purified

Sources & evidence

ORD record
ord-607f6f1ff01d48258ac969d71ceb447d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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