2-Aminobiphenyl → 3-Methylthio-7-phenylindolin-2-one

温度

-65 °C

A solution of 25.5 g. (0.15 mole) of 2-aminobiphenyl in 450 ml. of methylene chloride was cooled to -65° C. and treated with 20.1 g. (0.15 mole) of ethyl 2-methylthioacetate. Immediately 16.7 g. (0.155 mole) of t-butylhypochlorite was added dropwise over a 15 min. period while the temperature was maintained at -65° C. The reaction mixture was stirred at -65° C. for 1.5 hr., 15.5 g. (0.155 mole) of triethylamine was added, and the mixture was allowed to warm to ambient temperature. The solution was washed with two 100 ml. portions of water and then concentrated. The residue was mixed with 200 ml. of methanol, the mixture heated to reflux, 40 ml. of 3N hydrochloric acid was added and the mixture refluxed overnight. The solution was cooled and the resulting solid was collected by filtration, washed with methanol and recrystallized from benzene to yield 25.3 g. (66%) of product as tan needles, m.p. 164°-6° C.

1. additiontreated with 20.1 g
2. temperatureto warm to ambient temperature
3. washThe solution was washed with two 100 ml
4. concentrationportions of water and then concentrated
5. additionThe residue was mixed with 200 ml
6. temperatureof methanol, the mixture heated
7. temperatureto reflux
8. additionof 3N hydrochloric acid was added
9. temperaturethe mixture refluxed overnight
10. temperatureThe solution was cooled
11. filtrationthe resulting solid was collected by filtration
12. washwashed with methanol
13. customrecrystallized from benzene
14. customto yield 25.3 g

ORDレコード

ord-38121f6d39c245f092bf2293c59ce8cd

出典データセット

uspto-grants-1987_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04670566