تفاعل #814567

معادلة التفاعل

5-amino-4-cyano-3-methylthio-1-(2,4,6-trichlorophenyl)pyrazole

2-methoxyphenylmagnesium bromide

2-bromoanisole

magnesium

ammonium chloride

→

title compound

المردود 14.0%

5-Amino-4-(2-methoxybenzoyl)-3-methylthio-1-(2,4,6-trichlorophenyl)pyrazole

المردود 14.0%

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 16 hours
2. 2
   درجة الحرارةUpon cooling
3. 3
   استخلاصThe organic phase was extracted with aqueous hydrogen chloride
4. 4
   استخلاصthe acidic extract
5. 5
   workup.ADDITIONwas treated with 10 mL of concentrated hydrogen chloride
6. 6
   درجة الحرارةheated at 80°-90° C. for 10 minutes after which the mixture
7. 7
   درجة الحرارةwas cooled
8. 8
   استخلاصExtraction with methylene dichloride and chromatography of the extracts with mixtures of hexane and ethyl acetate

الإجراء التجريبي

To a solution of 2-methoxyphenylmagnesium bromide prepared from 18.7 g (0.10 mol) of 2-bromoanisole and 2.43 g (0.10 mol) of magnesium turnings in ether under dry nitrogen was added 1.6 g (5.0 mmol) of 5-amino-4-cyano-3-methylthio-1-(2,4,6-trichlorophenyl)pyrazole and the resulting mixture was stirred and refluxed for 16 hours. Upon cooling, the reaction was decomposed with 50 mL of saturated ammonium chloride solution. The organic phase was extracted with aqueous hydrogen chloride and the acidic extract was treated with 10 mL of concentrated hydrogen chloride and heated at 80°-90° C. for 10 minutes after which the mixture was cooled and made alkaline. Extraction with methylene dichloride and chromatography of the extracts with mixtures of hexane and ethyl acetate gave 313 mg (14%) of the title compound, m.p. 200°-202° C. Anal. Calcd. for C18H14O2 N3SCl3 : C, 48.82; H, 3.18; N, 9.49. Found: C, 48.54; H, 3.32; N, 9.09.

المصدر