71293-62-4 Usage
Preparation
STEP A:Preparation of 5-trifluoromethyl-3-methylthio-oxindole
To a solution of 15.4 g of p-trifluoromethylaniline in
400 ml. of methylene chloride cooled to minus 65℃. is
added dropwise a solution of 10.2 g of t-butyl hypo
chlorite in 20 ml. of methylene chloride. The solution is
stirred at minus 65℃. for 5 minutes and there is then
added dropwise 13.0 g of thioacetic acid ethyl ester in
20 ml of methylene chloride. The resulting mixture is
stirred at minus 65℃. for 30 minutes. There is then
slowly added 9.8 g of triethylamine and the reaction
mixture allowed to warm to room temperature at which
time 200 ml of 2 N. hydrochloric acid is added fol
lowed by stirring overnight at room temperature. There
is then added 20 ml of saturated sodium sulfite solution,
the mixture stirred for 15 minutes, the aqueous phase
separated and extracted into 1 N sodium hydroxide
solution and treated with 6 N. hydrochloric acid to
obtain a precipitate. The precipitate is then extracted
into methylene chloride, dried, filtered and the methy
lene chloride exchanged for ether and then pentane
added to obtain 5-trifluoromethyl-3-methylthio-oxin
dole, m.p. 136-138℃.STEP B: Preparation of 5-trifluoromethyl-oxindole
A mixture of 4.0 g of 5-trifluoromethyl-3-methylthio
oxindole, 20g of Raney Nickel and 100 ml. of methanol
is refluxed for 4 days, cooled, treated with methylene
chloride, filtered to remove the Raney Nickel and the
filtrate concentrated in vacuo to obtain 5-trifluorometh
yl-oxindole, m.p. 188-190℃.
Uses
5-(Trifluoromethyl)indolin-2-one is a useful reagent for the preparation of 3-Chloro-α-carbolines.
Check Digit Verification of cas no
The CAS Registry Mumber 71293-62-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,2,9 and 3 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 71293-62:
(7*7)+(6*1)+(5*2)+(4*9)+(3*3)+(2*6)+(1*2)=124
124 % 10 = 4
So 71293-62-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H6F3NO/c10-9(11,12)6-1-2-7-5(3-6)4-8(14)13-7/h1-3H,4H2,(H,13,14)
71293-62-4Relevant articles and documents
Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles
Dandia,Bhati,Jain,Sharma
experimental part, p. 1143 - 1147 (2012/03/10)
A simple facile, one-pot synthesis of oxindoles in reasonable purity is reported via intramolecular Friedal-Craft cyclization. Clay KSF is an inexpensive, efficient and mild catalyst for the synthesis of substituted oxindoles by the reaction of chloroacetyl chloride and various anilines under the influence of ultrasonic irradiation under solvent-free conditions. The remarkable advantages of this method are the simple experimental procedures, short reaction times, high yields of products, suitability for a wide variety of substituents, and the green aspects through the avoidance of toxic catalyst and solvents.
2-THIOINDOLES (SELENOINDOLES) AND RELATED DISULFIDES (SELENIDES) WHICH INHIBIT PROTEIN TYROSINE KINASES AND WHICH HAVE ANTITUMOR PROPERTIES
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, (2008/06/13)
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