1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86649902, compound

HRID 1803135Notes

Reaction equation

HRID 1803135 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])[N: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])[N: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 53404029HCID 53404029, compound

Product 1

HCID 86649902HCID 86649902, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step I (1): Dichloromethane (50 mL) was added to a flask charged with 3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)aniline (1.2 g, 5.85 mmol, N. Smith et. al PCT Publication WO 2003/077918) and 1,1′-thiocarbonyldipyridin-2(1H)-one (1.36 g, 5.85 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-methyl-1,2,4-oxadiazole (1.28 g, 5.18 mmol, 89% yield). LC-MS (M+H)+ 248.2.

Workup

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

Sources & evidence

ORD record
ord-1b332bba90f9405d9a9baf2bf1a8535a
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…