Potassium Carbonate → 6-Chloro-7-methylsulfanyl-2-(5-methyl-1,3,4-thiadiazol-2-ylsulfanyl)-3-trifluoromethylquinoxaline
Reaction equation
Cl[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([S:17][CH3:18])=[C:7]([Cl:16])[CH:8]=2)[N:3]=1.ClC1C=C2C(=CC=1SC)NC(=O)C(C(F)(F)F)=N2.CN(C1C=CC=CN=1)C.O=P(Cl)(Cl)Cl.[SH:51][C:52]1[S:53][C:54]([CH3:57])=[N:55][N:56]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[S:17][CH3:18])[N:3]=[C:2]([S:51][C:52]1[S:53][C:54]([CH3:57])=[N:55][N:56]=1)[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10]2Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2,6-Dichloro-7-methylsulfanyl-3-trifluoromethylquinoxaline (116 mg, 0.37 mmol, prepared similarly as described above from 6-chloro-7-methylsulfanyl-3-trifluoromethyl-1H-quinoxaline-2-one, dimethylaminopyridine and POCl3) and 2-mercapto-5-methyl-1,3,4-thiadiazole (146 mg, 1.1 mmol) was dissolved in DMF (3.3 ml). Potassium carbonate (20 mg) was added and the reaction mixture was stirred at 50° C. for 2 hours. The cooled mixture was partitioned between diethyl ether and water. The organic layer separated, evaporated and the residue recrystallised from ethanol to afford 80 mg (50%) of the title compound as a yellow solid.
Workup
- customThe cooled mixture was partitioned between diethyl ether and water
- customThe organic layer separated
- customevaporated
- customthe residue recrystallised from ethanol
Sources & evidence
- ORD record
- ord-64b49224fe134921ba28c9bc0156e74e
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06927214B1
Reaction notes
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