Deferiprone → 1,2-Dimethyl-4-oxo-1,4-dihydropyridin-3-yl 2,4-dinitrobenzenesulfonate

HRID 336108

反応式

HRID 336108 の反応式
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10].[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[S:23](Cl)(=[O:25])=[O:24])([O-:13])=[O:12]>N1C=CC=CC=1>[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[S:23]([O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10])(=[O:25])=[O:24])([O-:13])=[O:12]

参加物

4

反応物 2

HCID 2972DeferiproneHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-

生成物 1

HCID 866603571,2-Dimethyl-4-oxo-1,4-dihydropyridin-3-yl 2,4-dinitrobenzenesulfonate収率 23%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-Hydroxy-1,2-dimethylpyridin-4(1H)-one (0.10 g, 0.73 mmol) was reacted with 2,4-dinitrobenzenesulfonyl chloride (0.3 g, 1.1 mmol) in 10 mL of pyridine to afford PZBG-3d in 23% yield (0.07 g, 0.2 mmol). 1H NMR (400 MHz, CDCl3) δ=8.83 (d, J=2.8 Hz 1H), 8.37 (dd, J1=9.6 Hz, J2=2.8 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.03 (d, J=9.2 Hz, 1H), 6.25 (d, J=7.6 Hz, 1H), 3.68 (s, 3H), 2.31 (s, 3H). 13C NMR (100 MHz, CDCl3) δ=169.35, 154.98, 144.00, 142.61, 141.42, 140.76, 138.54, 129.69, 122.24, 118.15, 116.78, 59.63, 13.29.

後処理

  1. customto afford PZBG-3d in 23% yield (0.07 g, 0.2 mmol)

出典と根拠

ORDレコード
ord-b0e1cd454dc04576a8b0ece2525622cb
出典データセット
uspto-grants-2014_11
特許番号
US08889638B2

関連ノート

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