Reaction #312600

Reaction equation

hydrochloric acid

potassium carbonate

3,5-dichloro-1-methylpyrazole-4-carbohydroxamic acid

allyl bromide

→

aimed product

Yield 72.2%

N-allyloxy-3,5-dichloro-1-methylpyrazole-4-carboxylic acid amide

Yield 72.2%

Solvents

water

toluene

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   Otherprecipitated solid
3. 3
   Filtrationwas filtered off
4. 4
   Washwashed with water and toluene in that order
5. 5
   Otherdried

Procedure

In a solution of potassium carbonate (15.8 g, 114 mmol) in water (60 ml), a solution of 3,5-dichloro-1-methylpyrazole-4-carbohydroxamic acid (20.0 g, 95.2 mmol) and allyl bromide (13.8 g, 114 mmol) in toluene (60 ml) was added, and stirred at 50° C. for 3 hours. After cooling to room temperature, the mixture was adjusted to pH 1 by adding 35% hydrochloric acid, precipitated solid was filtered off, washed with water and toluene in that order, and dried to obtain the aimed product (17.2 g). Melting point 96-97° C. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.84 (s, 3H), 4.51 (d, J=6.3 Hz, 2H), 5.3-5.46 (m, 2H), 5.94-6.13 (m, 1H), 8.80 (brs, 1H).

Source