Morpholine → 3-(Morpholine-4-sulfonyl)benzoic acid

HRID 277575

Reaktionsgleichung

Reaktionsgleichung von HRID 277575
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>ClCCl>[N:23]1([S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531Diisopropylethylamine

Produkt 1

HCID 2574763-(Morpholine-4-sulfonyl)benzoic acidAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Commercially available 3-(chlorosulfonyl)benzoic acid (3 g, 13.5 mmol) was suspended in dichloromethane (50 mL). Diisopropylethylamine (5.19 mL, 30 mmol) and morpholine (1.67 mL, 21 mmol) were added slowly. After 2 h, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with 3N HCl three times. The ethyl acetate phase was dried over magnesium sulfate and the solvent was removed under reduced pressure, to provide the title product (2.97 g, 81%) as a white solid. 1HNMR (DMSO-d6) δ8.28 (d, J=8 Hz, 1H), 8.20 (s, 1H), 8.01 (d, 8 Hz, 1H), 7.83 (t, J=8 Hz, 1H), 3.91(m, 4H), 3.12 (M, 4H). MS (EI-NEG):[M+] 270.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 3N HCl three times
  4. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d49c8c3249fa4b67942e23d401120cdf
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355633B1

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