Morpholine → 4-[4-(Methylthio)benzoyl]morpholine

HRID 268601

Reaktionsgleichung

Reaktionsgleichung von HRID 268601
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.Cl.CN(C)CCN=C=NCC.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1COCC1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:9])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 832304-(Methylthio)benzoic acidHCID 57494384N-[2-(dimethylamino)ethyl]-N'-ethylcarbodiimide hydrochloride

Produkt 1

HCID 255722614-[4-(Methylthio)benzoyl]morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(methylthio)benzoic acid (6.76 g, 40.2 mmol) and N-[2-(dimethylamino)ethyl]-N′-ethylcarbodiimide hydrochloride (9.24 g, 48.2 mmol) in THF (100 mL) was added morpholine (4.2 mL, 48.2 mmol). After stirring for 2 hours, the reaction was concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and 2M hydrochloric acid (150 mL). The organic phase was separated, washed with 1M aqueous sodium carbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound LC retention time 3.52 mins MS m/z 238 (MH+).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (100 mL) and 2M hydrochloric acid (150 mL)
  3. customThe organic phase was separated
  4. washwashed with 1M aqueous sodium carbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-037be1b1b0ef41ba93b21ed6ef1338dd
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446117B2

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