4-Acetylbenzenesulphonamide → HCID 178419032、化合物

HRID 10738

反応式

HRID 10738 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].[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=3)[CH:27]=O)[N:21]=2)[CH2:16][CH2:15]1.C[O-].[Li+]>CN(C)C=O>[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26](/[CH:27]=[CH:2]/[C:1]([C:4]4[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=4)=[O:3])[CH:29]=3)[N:21]=2)[CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 178418754HCID 178418754、化合物

生成物 1

HCID 178419032HCID 178419032、化合物

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, 0.59 mmol) and 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-105B, 0.16 g, 0.59 mmol) in N,N-dimethylformamide (16 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The reaction mixture was allowed to stir for 18 hours at ambient temperature. The reaction was quenched with water. The aqueous solution was extracted with dichloromethane. The combined dichloromethane was concentrated. The crude product was purified by flash chromatography. Elution with methanol (10%, v/v, in dichloromethane) gave the title compound as red solid: m.p. 156–160° C. 1H NMR (DMSO-d6) δ 11.65 (bs, 1H), 8.32 (s, 1H), 8.19 (d, J=9.0 Hz, 2H), 8.00 (d, J=15.7 Hz, 1H), 7.95 (d, J=9.0 Hz, 2H), 7.62–7.52 (m, 2H), 7.24 (bs, 1H), 6.73 (s, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 1.98–1.94 (m, 1H), 0.88–0.85 (m 4H). MS m/z=454 ([M+H]+, 100%).

後処理

  1. customThe reaction was quenched with water
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. concentrationThe combined dichloromethane was concentrated
  4. customThe crude product was purified by flash chromatography
  5. washElution with methanol (10%, v/v, in dichloromethane)

出典と根拠

ORDレコード
ord-bc0bededacff4f5c853c190677c0df9b
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

関連ノート

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