Ethanol → N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamide

HRID 30552

반응식

HRID 30552 반응식
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[CH:15]=O)=[CH:6][CH:5]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][NH2:32])(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCO>O>[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14](/[CH:15]=[N:32]/[NH:31][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=3)(=[O:29])=[O:30])[CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 15303P-ToluenesulfonylhydrazideHCID 574358553-{[4-(Difluoromethoxy)phenyl]ethynyl}benzaldehyde

생성물 1

HCID 59790336N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamide수율 90.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 3-{[4-(difluoromethoxy)phenyl]ethynyl}benzaldehyde (3.69 g, 13.57 mmol), 4-methylbenzenesulfonohydrazide (2.9 g, 15.6 mmol) and EtOH (11 mL) was refluxed for 30 minutes. cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (Biotage) using hexanes/EtOAc (2/1) as the eluting solvents to give N′-[(1E)-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)methylene]-4-methylbenzenesulfonohydrazide as a tan solid (5.4 g, 90% yield), MS m/e (M+H)+ 441; 1H NMR (400 MHz, DMSO-d6) 2.32 (s, 3H), 7.2 (d, J=8.66 Hz, 2H), 7.3-7.6 (m, 8H), 7.72 (d, J=8.3 Hz, 2H), 7.88 (s, 1H), 11.54 (s, 1H).

후처리

  1. temperaturewas refluxed for 30 minutes
  2. extractionextracted with ethyl ether
  3. dry with materialThe organic extracts were combined dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified on silica gel (Biotage)

출처 및 근거

ORD 기록
ord-e652b03b300e43f696c6c99f5bd0173e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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