Tert-Butyl nitrite → HCID 68480474, compound

HRID 2404577Notes

Reaction equation

HRID 2404577 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:26][CH2:27][CH3:28])=[N:8][N:9]([C:12]2[CH:17]=[C:16]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:15]([CH3:24])=[CH:14][C:13]=2[F:25])[C:10]=1N)=[O:5])[CH3:2].N(OC(C)(C)C)=O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:26][CH2:27][CH3:28])=[N:8][N:9]([C:12]2[CH:17]=[C:16]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:15]([CH3:24])=[CH:14][C:13]=2[F:25])[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 68485221HCID 68485221, compound

Product 1

HCID 68480474HCID 68480474, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 1.48 g of ethyl-5-amino-3-ethoxy-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole-4-carboxylate was dissolved in 50 mL of tetrahydrofuran, and 0.44 g of tert-butyl nitrite was added under cooling with ice, followed by stirring at room temperature for 12 hours. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 1.18 g of ethyl-3-ethoxy-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole-4-carboxylate.

Workup

  1. temperatureunder cooling with ice
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-80b189df743e4b93a67f68cb14e735f8
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

Loading…