Succinic anhydride → HCID 4424586, compound

HRID 333113Notes

Reaction equation

HRID 333113 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1>O1CCOCC1>[O:20]=[C:14]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10](=[O:11])(=[O:12])[NH2:13])=[CH:8][CH:9]=1)[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 1696824-(2-Aminoethyl)benzenesulfonamide

Product 1

HCID 4424586HCID 4424586, compoundYield 92,000%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(2-aminoethyl)benzene sulfonamide (1 g, 5.0 mmol) and succinic anhydride (500 mg, 5.0 mmol) were combined in a round bottom flask containing dioxane (100 mL) and the slurry was heated to a reflux overnight. The white solid was filtered and washed with cold dioxane to yield the desired product (1.4 g, 4.6 mol, 92%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.71 (d, J=8.1 Hz, 2H), 7.36 (d, J=8.1 Hz, 2H), 7.38 (s, 1H), 3.26 (m, 2H), 2.75 (t, J=7.1 Hz, 2H), 2.5 (m, 2H), 2.3 (t, J=7.1 Hz, 2H); (M+H)+ (301).

Workup

  1. temperaturethe slurry was heated to a reflux overnight
  2. filtrationThe white solid was filtered
  3. washwashed with cold dioxane

Sources & evidence

ORD record
ord-62f5f786d9684018a65abaa13d1feb91
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

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