Reacción #312598

Ecuación de reacción

water

5-benzylthio-3-chloro-1-methylpyrazole-4-carboxylic acid chloride

allyloxyamine hydrochloride

triethylamine

→

desired product

Rendimiento 101.5%

(5-benzylthio-3-chloro-1-methylpyrazol-4-yl)-N-allyloxycarboxylic acid amide

Rendimiento 101.5%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added at 0° C.
2. 2
   workup.STIRRINGAfter stirring at room temperature for 1 hour
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off

Procedimiento

In a suspension of allyloxyamine hydrochloride (2.3 g, 21 mmol) in tetrahydrofuran (20 ml), 2.9 g (29 mmol) of triethylamine was added at 0° C., stirred at room temperature for 5 minutes and then a solution of 5-benzylthio-3-chloro-1-methylpyrazole-4-carboxylic acid chloride (2.1 g, 7.0 mmol) in tetrahydrofuran (10 ml) was added dropwise. After stirring at room temperature for 1 hour, water (100 ml) was added and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and the solvent was distilled off to obtain the desired product (2.4 g). Oily substance. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.45 (s, 3H), 4.11 (s, 2H), 4.53 (d, J=6.3 Hz, 2H), 5.34-5.45 (m, 2H), 6.00-6.13 (m, 1H), 7.03-7.06 (m, 2H), 7.24-7.28 (m, 3H), 9.14 (brs, 1H).

Fuente