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Methyl iodide → 1-Methyl-5-methylthio-3-(trifluoromethyl)pyrazole

HRID 1670368
Notes
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Reaction equation

HRID 1670368 reaction equation
[CH3:1][N:2]1[C:6](=[S:7])[CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[NH:3]1.[C:12](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH3:1][N:2]1[C:6]([S:7][CH3:12])=[CH:5][C:4]([C:8]([F:11])([F:9])[F:10])=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 190676872-Methyl-5-trifluoromethyl-2H-pyrazole-3-thiol

Product 1

HCID 593563841-Methyl-5-methylthio-3-(trifluoromethyl)pyrazoleYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.87 g of compound (8-5) and 4.40 g of potassium carbonate were suspended in 100 ml of acetonitrile. The suspension was stirred at room temperature for 15 minutes. A solution of 3.62 g of methyl iodide in 10 ml of acetonitrile was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure. After water was added to the residue, the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to produce 3.60 g of 1-methyl-5-methylthio-3-(trifluoromethyl)pyrazole (14).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionAfter water was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e735db6e981406bb4caae1efa0c81d8
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994094B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes