1,2-Dichloroethane → HCID 70972224, Verbindung

HRID 2409914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409914
[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9](O)=[O:10])=[CH:4][N:3]=[CH:2]1.Cl.CN.C(Cl)CCl.C1C=[N:26][C:25]2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CCOC(C)=O.CO.CN(C=O)C>[CH3:25][NH:26][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([C:5]2[O:1][CH:2]=[N:3][CH:4]=2)[CH:7]=1

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6364545Methylamine hydrochlorideHCID 71278133-(1,3-oxazol-5-yl)benzoic Acid

Produkt 1

HCID 70972224HCID 70972224, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

DMF (15.9 mL) was added to a round bottom flask containing 3-(oxazol-5-yl)benzoic acid (0.99 gm, 5.23 mmol), methylamine hydrochloride (0.39 gm, 5.76 mmol), EDC (1.10 gm, 5.76 mmol), and HOAt (0.78 gm, 5.76 mmol). DIPEA (2.29 mL, 13.08 mmol) was then added. The reaction mixture was stirred at rt overnight. After 24 h the mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes then 15% MeOH in EtOAc to give the product, N-methyl-3-(oxazol-5-yl)benzamide, (0.50 gm, 2.49 mmol, 48% yield) as a white solid. Anal. Calcd. for C11H10N2O2 m/z 202.1, found: 203.1 (M+H)+.

Aufarbeitung

  1. customAfter 24 h the mixture was partitioned between EtOAc and water
  2. customThe organic phase was isolated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified
  8. washeluting with a gradient of 0-100% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dfe440ed1c464e049ded24fa8671699f
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815909B2

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