Tetrahydrofuran → HCID 57712427, compound

HRID 1983053Notes

Reaction equation

HRID 1983053 reaction equation
[Cl:1][C:2]([Cl:20])([F:19])[S:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:8]=1N.O1CCCC1.N(OC(C)(C)C)=O>O>[Cl:20][C:2]([Cl:1])([F:19])[S:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10906Tert-Butyl nitriteHCID 23149166HCID 23149166, compound

Product 1

HCID 57712427HCID 57712427, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.04 g of 4-{[dichlorofluoromethyl]thio}-1-(4-methoxybenzyl)-1H-pyrazole-5-amine was dissolved to 20 ml of tetrahydrofuran. 1.55 g of t-butyl nitrite was added to the solution, followed by refluxed for 3 hours. After the reaction mixture was cooled to room temperature, water was added to the reaction mixture, and extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.94 g of 4-{[dichlorofluoromethyl]thio}-1-(4-methoxybenzyl)-1H-pyrazole.

Workup

  1. temperatureby refluxed for 3 hours
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-efeb9e234444491db013bdb1dea1239b
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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