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Potassium Carbonate → 6-Chloro-7-methylsulfanyl-2-(5-methyl-1,3,4-thiadiazol-2-ylsulfanyl)-3-trifluoromethylquinoxaline

HRID 584673
Notes
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Reaction equation

HRID 584673 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]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 218852-DimethylaminopyridineHCID 24813Phosphorus oxychlorideHCID 223411506-chloro-7-methylsulfanyl-3-trifluoromethyl-1H-quinoxalin-2-oneHCID 223411882,6-Dichloro-7-methylsulfanyl-3-trifluoromethylquinoxalineHCID 178434161HCID 178434161, compound

Product

1
HCID 223410966-Chloro-7-methylsulfanyl-2-(5-methyl-1,3,4-thiadiazol-2-ylsulfanyl)-3-trifluoromethylquinoxalineYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customThe cooled mixture was partitioned between diethyl ether and water
  2. customThe organic layer separated
  3. customevaporated
  4. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-64b49224fe134921ba28c9bc0156e74e
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06927214B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes