Reaction #312598

Reaction equation

water

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

allyloxyamine hydrochloride

triethylamine

→

desired product

Yield 101.5%

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

Yield 101.5%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

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

Procedure

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).

Source