4-Acetylbenzenesulphonamide → 4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

HRID 10736ノート

反応式

HRID 10736 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=O)[CH:15]([CH3:17])[CH3:16].C[O-].[Li+]>CN(C)C=O>[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27](/[CH:28]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[O:3])[CH:30]=1)[CH:15]([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 219810255-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

生成物 1

HCID 117544734-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.18 g, 0.62 mmol) in N,N-dimethylformamide (9 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The reaction was quenched with water. The aqueous solution was washed ethyl acetate, acidified to pH 5, extracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane). The combined dichloromethane and isopropyl alcohol was washed with brine, dried over sodium sulfate and concentrated. The crude product was then stirred in ethanol (50%, v/v, in acetone) to give the title compound as a light yellow solid: m.p.>240° C. 1H NMR (DMSO-d6) δ 8.60 (s, 1H), 8.26 (d, J=8.1 Hz, 2H), 8.06 (d, J=15.3 Hz, 1H), 8.07 (s, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.84 (d, J=15.3 Hz, 1H), 7.50 (s, 1H), 6.84 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 3.61 (d, J=7.3 Hz, 2H), 1.81–1.74 (m, 1H), 0.67 (d, J=16.7 Hz, 6H). MS m/z=471 ([M+H]+, 100%).

後処理

  1. customThe reaction was quenched with water
  2. washThe aqueous solution was washed ethyl acetate
  3. extractionextracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane)
  4. washThe combined dichloromethane and isopropyl alcohol was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. stirringThe crude product was then stirred in ethanol (50%, v/v, in acetone)

出典と根拠

ORDレコード
ord-96724e89cdcb4f12bbae30db440eb7ce
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

反応ノート

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