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

HRID 652258

반응식

HRID 652258 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-38121f6d39c245f092bf2293c59ce8cd
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670566

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