Hydrochloric Acid → 1,1-Difluoro-2-oxo-2-(4-vinylphenylamino)ethanesulfonyl fluoride

HRID 595781

반응식

HRID 595781 반응식
[F:1][S:2]([C:5]([F:10])([F:9])[C:6](F)=[O:7])(=[O:4])=[O:3].[CH:11]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)=[CH2:12].N1C=CC=CC=1.Cl>C(Cl)Cl>[F:9][C:5]([F:10])([S:2]([F:1])(=[O:4])=[O:3])[C:6](=[O:7])[NH:17][C:16]1[CH:18]=[CH:19][C:13]([CH:11]=[CH2:12])=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69614Difluoro(fluorosulphonyl)acetyl fluorideHCID 737004-Aminostyrene

생성물 1

HCID 867251551,1-Difluoro-2-oxo-2-(4-vinylphenylamino)ethanesulfonyl fluoride수율 96.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A 100 ml flask was charged with CH2Cl2 (24 ml) under nitrogen stream and stirred for 10 min at 0° C. and then 2-(fluorosulfonyl)difluoroacetyl fluoride (6.60 g, 37.6 mmol, 1.5 eq.) was added. After 20 minutes, the CH2Cl2 (12 ml) solution of 4-vinyl aniline (2.86 g, 24.4 mmol, 1.0 eq.) and pyridine (1.93 g, 24.4 mmol, 1.0 eq.) was added dropwise to the mixture over 10 minutes. The mixture was allowed to warm to RT and was stirred for 4 hours at RT. 1N HCl was added to the final reaction mixture and the lower layer was separated and washed with 1N HCl and brine. The solution was dried over MgSO4, filtrated and then CH2Cl2 was removed by an evaporator. The target compound was obtained as a white solid (6.57 g) in 96% yield. 1H NMR (400 MHz, CDCl3); delta=5.28 (d, J=10.9 Hz, 1H), 5.74 (d, J=17.6 Hz, 1H), 6.68 (dd, J=10.9, 17.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.7 Hz, 2H), 8.04 (brs, 1H). 19F-NMR (376 MHz, CDCl3, C6F6 as standard) delta=41.27 (t, J=4.6 Hz, 1F), −105.26 (d, J=4.2 Hz, 2F).

후처리

  1. waitAfter 20 minutes
  2. temperatureto warm to RT
  3. stirringwas stirred for 4 hours at RT
  4. customreaction mixture
  5. customthe lower layer was separated
  6. washwashed with 1N HCl and brine
  7. dry with materialThe solution was dried over MgSO4
  8. filtrationfiltrated
  9. customCH2Cl2 was removed by an evaporator

출처 및 근거

ORD 기록
ord-72c94bd7bd4a476eade843960aa57c28
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09244345B1

연결된 노트

불러오는 중…