4-Acetylbenzenesulphonamide → 4-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamide

HRID 347369ノート

反応式

HRID 347369 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].[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][C:17]=1[CH:18]=O.C[O-].[Li+]>CN(C)C=O.O>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][C:17]=1/[CH:18]=[CH:2]/[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[O:3]

参加物

6

反応物 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 210825102,4-Dimethoxy-5-pyrrolidin-1-ylbenzaldehyde

生成物 1

HCID 694900494-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamide収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Ex-48A: To a solution of 4-acetylbenzenesulfonamide (Ex-35A, 0.13 g, 0.64 mmol) and 2,4-dimethoxy-5-pyrrolidin-1-yl-benzaldehyde (Ex-38B, 0.15 g, 0.64 mmol) in N,N-dimethylformamide (5 mL) was added lithium methoxide (1.0 M in methanol, 1.6 mL, 1.6 mmol). The solution was allowed to stir at ambient temperature for 13 h and then at 40° C. for 2 h. HPLC indicated no further change of starting materials. The reaction mixture was then diluted with water, acidified to pH 5. The resulting precipitate was collected by filtration, washed with water, dried in vacuo. The crude product was slurried in ethanol overnight. The solid was collected by filtration, washed with ethanol, dried in vacuo to give 4-[3E-(2,4-dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonamide (0.16 g, 59%) as a red solid, m.p. 220–222° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.22 (d, J=8.7 Hz, 2H), 8.04 (d, J=16.1 Hz, 1H), 7.93 (d, J=8.7 Hz, 2H), 7.64 (d, J=16.1 Hz, 1H), 7.52 (s, 2H), 7.18 (s, 1H), 6.67 (s, 1H), 3.86 (s, 6H), 3.19–3.17 (m, 4H), 1.84–1.83 (m, 4H). HRMS Calcd for C21H24N2O5S: 416.1408 (M+); Found: 416.1408.

後処理

  1. waitat 40° C. for 2 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo
  5. waitThe crude product was slurried in ethanol overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with ethanol
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-8d711ecda1e64cf9bdaaec9708ec8622
出典データセット
uspto-grants-2007_02
特許番号
US07173129B2

反応ノート

読み込み中…