Ethyl 3-ethoxy-3-iminopropionate hydrochloride → Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate

HRID 631050

Reaktionsgleichung

Reaktionsgleichung von HRID 631050
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].Cl.C(O[C:10](=N)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])C>>[NH2:5][C:3]1[S:4][C:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:1][N:2]=1

Komponenten

3

Edukt 2

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 2723789Thiosemicarbazide

Produkt 1

HCID 292304Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetateAusbeute 47 %

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Thiosemicarbazide (1.0 g, 11.0 mmol) and ethyl 3-ethoxy-3-iminopropionate hydrochloride (2.0 g, 10.0 mmol) were mixed in glacial acid (2 mL) for 10 min at 55° C. and then boiled for 1.5 h. The reaction mixture was evaporated, diluted with cold water, carefully neutralized with NaHCO3, and cooled to 5° C. The precipitate was collected and crystallized from water to yield 0.88 g (4.70 mmol, 47%) of the product, mp 149-150° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.19 (t, 3H, J=7.2 Hz), 3.96 (s, 2H), 4.10 (q, 2H, J=6.9 Hz), 7.11 (s, 2H); 13C NMR (75 MHz, DMSO-d6) δ 14.0, 35.4, 60.9, 150.4, 168.9, 169.6.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additiondiluted with cold water
  3. customThe precipitate was collected
  4. customcrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-c35730d6175f415182ab9fe957aec0f7
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320734B2

Verknüpfte Notizen

Wird geladen…