1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86640997, compound

HRID 1876015Notes

Reaction equation

HRID 1876015 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[CH3:28])[CH:24]=[N:23][C:22]([NH2:29])=[CH:21]2.[CH3:30][C:31]1[C:40]([CH3:41])=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[C:34]([NH2:42])[N:35]=[CH:36]2>ClCCl>[N:29]([C:22]1[N:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[CH:19][C:18]([CH3:17])=[C:27]([CH3:28])[CH:26]=2)=[C:1]=[S:2].[N:42]([C:34]1[N:35]=[CH:36][C:37]2[C:32]([CH:33]=1)=[C:31]([CH3:30])[C:40]([CH3:41])=[CH:39][CH:38]=2)=[C:1]=[S:2]

Participants

6

Reactant 3

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 59286677HCID 59286677, compoundHCID 66724741HCID 66724741, compound

Product 2

HCID 59286633HCID 59286633, compoundHCID 86640997HCID 86640997, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (1.35 g, 5.81 mmol) in dichloromethane (19 mL) at ambient temperature was added a mixture (2:1) of 6,7-dimethylisoquinolin-3-amine and 5,6-dimethylisoquinolin-3-amine (1.00 g, 5.81 mmol). The reaction mixture was placed into a preheated oil-bath and stirred at 40° C. for 18 h, then cooled, concentrated, and purified by silica gel chromatography (10-35% ethyl acetate in hexanes) to afford a mixture (2:1) of 3-isothiocyanato-6,7-dimethylisoquinoline and 3-isothiocyanato-5,6-dimethylisoquinoline (186 mg, 0.869 mmol, 15%) as a yellow solid. MS (LC/MS) R.T.=2.06; [M+H]+=215.1.

Workup

  1. customThe reaction mixture was placed into a preheated oil-bath
  2. temperaturecooled
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (10-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a07cf98118d644a78f7d19721ca77075
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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