Ammonia → 1-Acetylindoline-5-sulfonamide

HRID 528819

Reaktionsgleichung

Reaktionsgleichung von HRID 528819
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 8042081-Acetylindoline-5-sulfonamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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×)

Quellen und Nachweise

ORD-Eintrag
ord-ac4d14f516a44c16932ecae86cb3b77f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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