Ethanethiol → HCID 67134132, compound

HRID 222548Notes

Reaction equation

HRID 222548 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([SH:9])[CH3:8].Cl[C:11]1[C:20]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[C:19]([CH3:32])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1>CN(C=O)C.O>[CH2:7]([S:9][C:11]1[C:20]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[C:19]([CH3:32])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:8]

Participants

6

Reactant 3

HCID 6343Ethanethiol2×HCID 11430Potassium Carbonate2×HCID 86645383HCID 86645383, compound

Product 1

HCID 67134132HCID 67134132, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2.1 g (15.4 mmol) of K2CO3 and 760 μl (10.3 mmol) of ethanethiol were added in succession to a solution of 2.1 g (5.1 mmol) of 2-(2-chloro-4-methylquinolin-3-yl)isoindoline-1,3-dione in DMF (36 ml). The mixture was then heated for 16 h at 60° C. A further 2.1 g (15.4 mmol) of K2CO3 and 760 μl (10.3 mmol) of ethanethiol were then added, and the mixture was again heated for 16 h at 50° C. After cooling to RT, the mixture was diluted with water and extracted twice with EA. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. There were obtained as residue 1.7 g (4.0 mmol, 78%) of 2-(2-(ethylthio)-4-methylquinolin-3-yl)isoindoline-1,3-dione, which was reacted further without additional purification.

Workup

  1. temperaturethe mixture was again heated for 16 h at 50° C
  2. temperatureAfter cooling to RT
  3. extractionextracted twice with EA
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d53b6abb6144ea298b75691c70ac2b3
Source dataset
uspto-grants-2012_06
Patent number
US08207342B2

Reaction notes

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