Ammonia → 1-Acetylindoline-5-sulfonamide

HRID 528819

反応式

HRID 528819 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].N.CC[N:20](CC)CC>C(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:20])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 140245961-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

生成物 1

HCID 8042081-Acetylindoline-5-sulfonamide収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution 1-acetylindoline-5-sulfonyl chloride (Borror, A. L. et al., J. Org. Chem., 53:2047-2052 (1988)) (2.00 g, 7.70 mmol) in CH2Cl2 (5.0 mL) was added NH3 (38.5 mL, 19.3 mmol, 0.5M solution in dioxane) and Et3N (2.2 mL, 15.4 mmol). The resulting reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then concentrated in vacuo, and the residue was triturated with 1N aq. HCl solution (2×) and water (1×) to give the title compound (1.80 g, 97%) as a white solid. 1H NMR (DMSO-d6) δ 8.11 (d, J=8.1 Hz, 1H), 7.64-7.62 (m, 2H), 7.20 (br s, 2H), 4.16 (t, J=8.6 Hz, 2H), 3.19 (t, J=8.5 Hz, 2H), 2.19 (s, 3H); MS(ESI+) m/z 241.0 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue was triturated with 1N aq. HCl solution (2×) and water (1×)

出典と根拠

ORDレコード
ord-ac4d14f516a44c16932ecae86cb3b77f
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

関連ノート

読み込み中…