Benzenesulfonyl chloride → N-(3-(3-(1,3-dioxoisoindolin-2-yl)propyl)phenyl)benzenesulfonamide

HRID 716791Notes

Reaction equation

HRID 716791 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[O:21]=[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[N:11]1[CH2:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([NH:1][S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 221249642-(3-(3-Aminophenyl)propyl)isoindoline-1,3-dione

Product 1

HCID 68524682N-(3-(3-(1,3-dioxoisoindolin-2-yl)propyl)phenyl)benzenesulfonamide

Procedure

Sulfonation of 2-(3-(3-aminophenyl)propyl)isoindoline-1,3-dione by benzenesulfonyl chloride following the method used in Example 6 gave N-(3-(3-(1,3-dioxoisoindolin-2-yl)propyl)phenyl)benzenesulfonamide as a yellow semi-solid. Yield (0.80 g, 62%). 1H NMR (400 MHz, DMSO-d6) δ 10.18 (s, 1H), 7.87-7.81 (m, 4H), 7.72 (d, J=7.6 Hz, 2H), 7.58-7.49 (m, 3H), 7.11 (t, J=8.0, 1H), 6.92 (s, 1H), 6.88-6.85 (m, 2H), 3.52 (t, J=7.2 Hz, 2H), 2.50-2.49 (m, 2H), 1.81-1.74 (m, 2H).

Sources & evidence

ORD record
ord-53243fa8ce4145d8b78815383188315a
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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