Reacción #1379688

Ecuación de reacción

potassium carbonate

4-methoxyimino-5-methylthiochroman-6-carboxylic acid-1,1-dioxide

1-ethyl-5-hydroxypyrazol

→

4-methoxyimino-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide

Rendimiento 72.9%

Disolventes

t-amyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto react at 90° C. for 8 hours
2. 2
   OtroAfter the reaction
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   workup.ADDITIONethyl acetate was added
5. 5
   Extracciónthe mixture was extracted with a 5% potassium carbonate aqueous solution
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   LavadoThe extract was washed with a saturated sodium hydroxide aqueous solution
8. 8
   Secadodried over sodium sulfate
9. 9
   Concentraciónconcentrated

Procedimiento

0.9 Gram (3.2 mmol) of the 4-methoxyimino-5-methylthiochroman-6-carboxylic acid-1,1-dioxide and 0.44 g (3.9 mmol) of 1-ethyl-5-hydroxypyrazol were dissolved in 5 ml of t-amyl alcohol, and 0.81 g (3.9 mmol) of DCC(dicyclohexyl-carbodiimide) was added at room temperature. The mixture was stirred at room temperature for 2 hours, then, 0.74 g (5.4 mmol) of potassium carbonate was added, and the mixture was allowed to react at 90° C. for 8 hours. After the reaction, the solvent was distilled off, ethyl acetate was added, and the mixture was extracted with a 5% potassium carbonate aqueous solution. An aqueous layer was neutralized with concentrated hydrochloric acid, and extracted with ethyl acetate. The extract was washed with a saturated sodium hydroxide aqueous solution, dried over sodium sulfate and concentrated to give 0.88 g (yield 72%) of 4-methoxyimino-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide.

Fuente