Dimethylamine → N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamide

HRID 2109735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109735
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1.[CH3:12][NH:13][CH3:14]>C1COCC1>[CH3:12][N:13]([CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1)[CH3:14]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 819632-Acetamido-4-chloromethylthiazole

Produkt 1

HCID 57634222N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(4-(Chloromethyl)thiazol-2-yl)acetamide (2.0 g, 10 mmol) in 20 mL THF was added in portions to dimethylamine (4.7 g, 105 mmol). After addition, the mixture was stirred for an additional 30 minutes. The solvent was removed under reduced pressure. 200 mL distilled water was then added to the resulting residue, and the mixture was extracted with EtOAc. The EtOAc solution was washed with brine solution and dried over sodium sulfate. After removing the solvent, an off-white solid was obtained as the crude product (1.3 g, yield=80%). LCMS (API-ES) m/z (%) 200.1 (100%, M++H). 1H NMR (400 MHz, CDCl3) δ ppm 2.24 (s, 3H) 2.26 (s, 6H) 3.43 (s, 2H) 6.73 (s, 1H).

Aufarbeitung

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. distillation200 mL distilled water
  4. additionwas then added to the resulting residue
  5. extractionthe mixture was extracted with EtOAc
  6. washThe EtOAc solution was washed with brine solution
  7. dry with materialdried over sodium sulfate
  8. customAfter removing the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b01963d22d2e4c539c0571cedb6f8680
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514566B2

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