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

HRID 1803144Notes

Reaction equation

HRID 1803144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=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]([C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=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 584144723-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

Product 1

HCID 866499074-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazoleYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step K (3): Dichloromethane (25 mL) was added to a flask charged with 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline (1.5 g, 7.38 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (2.57 g, 11.1 mmol). The resulting mixture was stirred for 16 h at rt. The reaction mixture was concentrated in vacuo. The crude products were purified using silica gel chromatography (30% EtOAc/dichloromethane). The fractions containing product were combined and concentrated. The resulting solid was recrystallized from hexane to afford 4-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazole (1.46 g, 5.95 mmol, 81% yield) as a light yellow solid. LC-MS (M+H)+ 272.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.57 (d, J=1.83 Hz, 1 H) 7.07 (d, J=1.53 Hz, 1 H) 6.94-7.04 (m, 2 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude products were purified
  3. additionThe fractions containing product
  4. concentrationconcentrated
  5. customThe resulting solid was recrystallized from hexane

Sources & evidence

ORD record
ord-33ad8e97349443d497fd61178c7f1cbf
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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