1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86649900, compound

HRID 1803133Notes

Reaction equation

HRID 1803133 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH: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]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[CH: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 66859388HCID 66859388, compound

Product 1

HCID 86649900HCID 86649900, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step H (3): Dichloromethane (20 mL) was added to a flask charged with 3-methoxy-4-(3-methylisoxazol-5-yl)aniline (500 mg, 2.448 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (569 mg, 2.448 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 (20-50% EtOAc/hexane) linear gradient to afford 5-(4-isothiocyanato-2-methoxyphenyl)-3-methylisoxazole (0.510 g, 84% yield). LC-MS (M+H)+ 247.2. 1H NMR (400 MHz, methanol-d4) δ ppm 7.86 (d, J=8.56 Hz, 1 H) 7.06 (d, J=2.01 Hz, 1 H) 6.99 (dd, J=8.44, 1.89 Hz, 1 H) 6.73 (s, 1 H) 3.97 (s, 3 H) 2.31 (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-5a0aad02ea944436a2b5b0ea7ae89915
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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