Hydrogen Peroxide → HCID 89871761, compound

HRID 929286Notes

Reaction equation

HRID 929286 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:19][CH3:20])[C:8](=[O:18])[CH2:9][CH2:10][S:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:5][N:4]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:3]=1.[OH:27]O>FC(F)(F)C(O)C(F)(F)F>[Cl:1][C:2]1[C:6]([N:7]([CH2:19][CH3:20])[C:8](=[O:18])[CH2:9][CH2:10][S:11]([CH2:12][CH2:13][C:14]([F:16])([F:15])[F:17])=[O:27])=[CH:5][N:4]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86700627Tyclopyrazoflor

Product 1

HCID 89871761HCID 89871761, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I) (500 mg, 1.229 mmol) in hexafluoroisopropanol (5 mL) stirring at room temperature was added 30% hydrogen peroxide (523 mg, 4.92 mmol). The solution was stirred at room temperature for 15 minutes. It was quenched with saturated sodium sulfite solution and extracted with CH2Cl2. Silica gel chromatography (0%-10% MeOH/CH2Cl2) gave the title compound as white semi-solid (495 mg, 95%): IR (thin film) 1660 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.96 (d, J=2.4 Hz, 1H), 8.64 (dd, J=4.7, 1.4 Hz, 1H), 8.07-8.00 (m, 2H), 7.46 (ddd, J=8.3, 4.8, 0.7 Hz, 1H), 3.85-3.61 (m, 2H), 3.23-3.08 (m, 1H), 3.03-2.76 (m, 3H), 2.74-2.52 (m, 4H), 1.18 (t, J=7.2 Hz, 3H); ESIMS m/z 423 ([M+H]+).

Workup

  1. customIt was quenched with saturated sodium sulfite solution
  2. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-2485d9f30d8a423885c8b43250eefccb
Source dataset
uspto-grants-2016_03
Patent number
US09295258B2

Reaction notes

Loading…