Ammonia → 1-Acetylindoline-5-sulfonamide

HRID 528819

반응식

HRID 528819 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 8042081-Acetylindoline-5-sulfonamide수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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×)

출처 및 근거

ORD 기록
ord-ac4d14f516a44c16932ecae86cb3b77f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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