Ammonia → 1-Acetylindoline-5-sulfonamide

HRID 528819

Reaction equation

HRID 528819 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 8042081-Acetylindoline-5-sulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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×)

Sources & evidence

ORD record
ord-ac4d14f516a44c16932ecae86cb3b77f
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Linked notes

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