2-Phenylbutyric Acid → 4'-(1-Oxo-2-phenylbutyl)methanesulfonanilide

HRID 1414266

반응식

HRID 1414266 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:3].[C:12]1([CH:18]([CH2:22][CH3:23])[C:19](O)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[O:20]=[C:19]([C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=1)[CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:22][CH3:23]

참가 물질

4

반응물 2

HCID 70122-Phenylbutyric AcidHCID 70970Methanesulfonamide, N-phenyl-

생성물 1

HCID 214866524'-(1-Oxo-2-phenylbutyl)methanesulfonanilide수율 23%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Methanesulfonanilide (40 g., 0.234 mole) is added over a 10 minute period with stirring to polyphosphoric acid (400 g.) heated to 90°-100°C. Heating and stirring are continued for additional 10 minutes, at which time 2-phenylbutanoic acid (36.0 g., 0.219 mole) is added portionwise during 20 minutes. After heating and stirring for 10 minutes, the solution is poured into water (600 ml.) and ice (400 g.) with stirring. The water is decanted and ethyl ether (200 ml.) is added to the remaining oil with stirring. After cooling in ice water, the product crystallizes and is collected: 18.4 g., m.p. 143°-147°C. Recrystallization from isopropanol yields 15.7 g. (23% yield), m.p. 148°-150°C.

후처리

  1. temperatureheated to 90°-100°C
  2. temperatureHeating
  3. additionis added portionwise during 20 minutes
  4. temperatureAfter heating
  5. stirringstirring for 10 minutes
  6. stirringwith stirring
  7. customThe water is decanted
  8. additionethyl ether (200 ml.) is added to the remaining oil
  9. stirringwith stirring
  10. temperatureAfter cooling in ice water
  11. customthe product crystallizes
  12. customis collected
  13. customRecrystallization from isopropanol
  14. customyields 15.7 g

출처 및 근거

ORD 기록
ord-58cc82de06ba4bb5a678ac389eed67c7
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04001229

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