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

HRID 30552

反応式

HRID 30552 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e652b03b300e43f696c6c99f5bd0173e
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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