Reaction #312602

Reaction equation

hydrochloric acid

potassium carbonate

5-benzylthio-1-methylpyrazole-4-carbohydroxamic acid

allyl bromide

→

aimed product

Yield 82.4%

N-allyloxy-5-benzylthio-1-methylpyrazole-4-carboxylic acid amide

Yield 82.4%

Solvents

water

toluene

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe resulting ethyl acetate solution was washed with water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off

Procedure

In a solution of potassium carbonate (1.3 g, 9.4 mmol) in water (10 ml), a solution of 5-benzylthio-1-methylpyrazole-4-carbohydroxamic acid (2.0 g, 7.6 mmol) and allyl bromide (1.1 g, 9.1 mmol) in toluene (10 ml) were added, and stirred at 50° C. for 4 hours. After cooling to room temperature, the mixture was adjusted to pH 1 by adding 35% hydrochloric acid and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the aimed product (1.9 g). Oily substance. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.42 (s, 3H), 3.95 (s, 2H), 4.49 (d, J=6.3 Hz, 2H), 5.33-5.43 (m, 2H), 6.00-6.16 (m, 1H), 6.93-7.00 (m, 2H), 7.21-7.30 (m, 3H), 8.08 (s, 1H), 9.68 (brs, 1H).

Source