Morpholine → (3,4-Dinitrophenyl)(morpholino)methanone

HRID 1047550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047550
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN(C=O)C.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:9])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 107093,4-Dinitrobenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 13043973(3,4-Dinitrophenyl)(morpholino)methanoneAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3,4-dinitrobenzoic acid (200 mg, 0.943 mmol) and DMF (2 drops) in THF (7 mL) was treated with thionyl chloride (0.14 mL, 224 mmol) and then heated at reflux for 2.5 h. The mixture was cooled to 0° C. and triethylamine (286 mg, 1.883 mmol) was added over 25 min while keeping the internal temperature at 0° C. Morpholine (164 mg, 1.883 mmol) was added. The mixture was stirred overnight and allowed to warm to ambient temperature. Purification by flash chromatography afforded the title compound (150 mg). 1H NMR (400 MHz, CD3OD): δ 8.36 (s, 1H), 8.10 (d, 1H, J=8.8 Hz), 7.28 (d, 1H, J=9.2 Hz), 3.79 (m, 4H), 3.16 (m, 4H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. customat 0° C
  4. temperatureto warm to ambient temperature
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7d6739403c8740dca5da36cf7d61bf52
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569511B2

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