1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 82007988, compound

HRID 1803165Notes

Reaction equation

HRID 1803165 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[C:11](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:12]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:11]=[S:12])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 70182544-Bromo-3-methoxyaniline

Product 1

HCID 82007988HCID 82007988, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step P (1): To a solution of 4-bromo-3-methoxyaniline (0.500 g, 2.48 mmol) in dichloromethane (10 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.575 g, 2.48 mmol). The resulting mixture was stirred at rt for 3 h. The crude reaction mixture was loaded onto silica gel and purified using silica gel chromatography (3-60% EtOAc/hexanes, linear gradient) to afford 1-bromo-4-isothiocyanato-2-methoxybenzene (0.48 g, 75% yield) as an off white solid. LC-MS (M+H)+ 244.0. 1H NMR (400 MHz, methanol-d4) δ ppm 7.53 (d, J=8.56 Hz, 1 H) 6.94 (d, J=2.27 Hz, 1 H) 6.79 (dd, J=8.56, 2.27 Hz, 1 H) 3.86 (s, 3 H).

Workup

  1. customThe crude reaction mixture
  2. custompurified

Sources & evidence

ORD record
ord-59bd9306619f4c0b8ffa0f2ccb0dd818
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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