1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86649894, compound

HRID 1803121Notes

Reaction equation

HRID 1803121 reaction equation
[Cl:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[O:14][CH3:15])[N:3]=1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[Cl:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([N:11]=[C:16]=[S:17])=[CH:9][C:8]=2[O:14][CH3:15])[N:3]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 58075503HCID 58075503, compound

Product 1

HCID 86649894HCID 86649894, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step E (4): Dichloromethane (25 mL) was added to a flask charged with 4-(3-chloro-1H-1,2,4-triazol-1-yl)-3-methoxyaniline (0.577 g, 2.57 mmol) and 1,1′-thiocarbonyldi-2(1H)-pyridone (0.597 g, 2.57 mmol). The resulting mixture was stirred for 24 h at rt. The crude reaction mixture concentrated in vacuo and the crude product was purified using silica gel chromatography (0-5% EtOAc/chloroform, linear gradient) to afford 3-chloro-1-(4-isothiocyanato-2-methoxyphenyl)-1H-1,2,4-triazole (529 mg, 1.983 mmol, 77% yield) as a off-white solid. LC-MS (M+H)+ 267.1. 1H NMR (500 MHz, chloroform-d) δ ppm 8.67 (s, 1 H) 7.79 (d, J=8.55 Hz, 1 H) 6.98 (dd, J=8.70, 1.98 Hz, 1 H) 6.91 (d, J=1.83 Hz, 1 H) 3.97 (s, 3 H).

Workup

  1. customThe crude reaction mixture
  2. concentrationconcentrated in vacuo
  3. customthe crude product was purified

Sources & evidence

ORD record
ord-30191cd44efe4125aab4c67384d291bd
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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