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

HRID 652258

Reaktionsgleichung

Reaktionsgleichung von HRID 652258
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC[C:16](OCC)=[S:17].[C:21]([O:25]Cl)(C)(C)[CH3:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][S:17][CH:22]1[C:7]2[C:2](=[C:3]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:4]=[CH:5][CH:6]=2)[NH:1][C:21]1=[O:25]

Komponenten

6

Edukt 4

HCID 70152-AminobiphenylHCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetate

Produkt 1

HCID 133019753-Methylthio-7-phenylindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-38121f6d39c245f092bf2293c59ce8cd
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670566

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