| Identification | More | [Name]
5-Trifluoromethyl-2-oxindole | [CAS]
71293-62-4 | [Synonyms]
5-(TRIFLUOROMETHYL)OXINDOLE
5-(Trifluoromethyl)-2-oxoindole
5-(Trifluoromethyl)oxindole 97%
5-(Trifluoromethyl)oxindole97%
5-(TRIFLUOROMETHYL)OXINDOLE ,98% | [Molecular Formula]
C9H6F3NO | [MDL Number]
MFCD02179602 | [Molecular Weight]
201.15 | [MOL File]
71293-62-4.mol |
| Questions And Answer | Back Directory | [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℃. |
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