Ammonia tetrahydrofuran → 4-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonamide

HRID 1483836Notes

Reaction equation

HRID 1483836 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:14][CH2:13]1.[NH3:22].C1COCC1>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([S:18]([NH2:22])(=[O:20])=[O:19])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 21982362Ammonia tetrahydrofuranHCID 893896834-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonyl chloride

Product 1

HCID 712276614-(1,3-Dioxoisoindolin-2-yl)cyclohexane-1-sulfonamideYield 64%

Procedure

A mixture of 4-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-sulfonyl chloride (5 g, 15.2 mmol) in NH3/THF (150 mL) was stirred at room temperature overnight. The mixture was concentrated in vacuo. The residue was dissolved into about 100 mL of hot water and the solid was filtered under hot condition. The filtrate was concentrated in vacuo to give 4-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-sulfonamide (3 g, 64%) as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved into about 100 mL of hot water
  3. filtrationthe solid was filtered under hot condition
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a6f1d9add9f54c7b9d6fa704e2e9d1d0
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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