1,1'-Thiocarbonyldi-2(1H)-pyridone → 1-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

HRID 1803106Notes

Reaction equation

HRID 1803106 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[C:6]([O:15][CH3:16])=[CH:5][C:3]=1[NH2:4].[C:17](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:18]>ClCCl>[F:1][C:2]1[C:3]([N:4]=[C:17]=[S:18])=[CH:5][C:6]([O:15][CH3:16])=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[CH:8]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 580756292-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

Product 1

HCID 866498891-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazoleYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step B (3): Dichloromethane (125 mL) was added to a flask charged with 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (1.07 g, 4.82 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (1.12 g, 4.82 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 over 36 min, flow 25 mL/min) to afford 1-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (950 mg, 75% yield) as a yellow solid. LC-MS (M+H)+ 265.1. 1H NMR (500 MHz, chloroform-d) δ ppm 8.74 (s, 1 H) 7.75 (d, J=10.07 Hz, 1 H) 6.84 (d, J=6.41 Hz, 1 H) 3.94 (s, 3 H) 2.48 (s, 3 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was purified
  3. customsilica gel chromatography (0-5% EtOAc/chloroform, linear gradient over 36 min, flow 25 mL/min)

Sources & evidence

ORD record
ord-d734587cbb674db78f75aedea70dea75
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…