Pyridine → N-3-Quinolinylbenzenesulfonamide

HRID 394554ノート

反応式

HRID 394554 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(OCC)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:1][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH:3]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 113753-Aminoquinoline

生成物 1

HCID 16654646N-3-Quinolinylbenzenesulfonamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-aminoquinoline (7.2 g, 50 mmol) in acetonitrile (150 mL) was added pyridine (25 mL) and the resulting mixture was cooled to 0° C. A solution of benzenesulfonyl chloride (7 mL, 55 mmol) in acetonitrile (20 mL) was added dropwise over 30 minutes. The mixture was allowed to warm to rt and stirred for 18 hours. The mixture was diluted with ethyl acetate (100 mL) and washed successively with 1N HCl, brine and saturated CuSO4, dried (MgSO4), and concentrated in vacuo to afford an oil. Purification by flash silica gel column chromatography eluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid. MS; (M+H)+=285

後処理

  1. temperatureto warm to rt
  2. washwashed successively with 1N HCl, brine and saturated CuSO4
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customPurification by flash silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid

出典と根拠

ORDレコード
ord-be7dfc7e9e8c4e32b0ec01ae27d2bc73
出典データセット
uspto-grants-2003_08
特許番号
US06602883B1

反応ノート

読み込み中…