2-(1,3-Dioxolanyl)-3-aminopyridine → 2-((3-Aminopyridin-2-yl)methylene)hydrazinecarbothioamide

HRID 863570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863570
O1CCO[CH:2]1[C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1.[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>C(O)C.O.Cl>[NH2:12][C:11]1[C:6]([CH:2]=[N:13][NH:14][C:15]([NH2:17])=[S:16])=[N:7][CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 2

HCID 3293632-(1,3-Dioxolanyl)-3-aminopyridineHCID 2723789Thiosemicarbazide

Produkt 1

HCID 30063152-((3-Aminopyridin-2-yl)methylene)hydrazinecarbothioamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-(1,3-dioxolanyl)-3-aminopyridine (0.80 g, 4.8 mmol) in 10 mL of ethanol, 8 mL of water and 2 mL of concentrated hydrochloric acid was added 0.48 g (5.3 mmol) of thiosemicarbazide. The mixture was stirred at room temperature overnight and refluxed for 1 h, cooled and filtered. The crude yellow hydrochloride salt was dissolved in 50 mL of hot water and filtered. To the hot filtrate was added 10 mL of 5% sodium bicarbonate solution. The mixture was stirred at room temperature for 1 h, filtered and washed with water, followed by ethanol to yield 3-amino-2-formylpyridine thiosemicarbazone. Yield: 0.72 g (77%); mp 240°-241° C. dec; MS m/e 194 (M+); 1H NMR (90 MHz, DMSO-d6) δ 6.48 (br s, 2H, 3-NH2, D2O exchangeable), 7.12 (m, 2H, 4-H and 6-H), 7.83 (dd, 1H, 5-H), 8.10 (br s, 2H, CSNH2, D2O exchangeable), 8.10 (s, 1H, 2-CH), 10.95 (s, 1H, NNH, D2O exchangeable). Anal. (C7H9N5S) C, H, N.

Aufarbeitung

  1. temperaturerefluxed for 1 h
  2. temperaturecooled
  3. filtrationfiltered
  4. dissolutionThe crude yellow hydrochloride salt was dissolved in 50 mL of hot water
  5. filtrationfiltered
  6. additionTo the hot filtrate was added 10 mL of 5% sodium bicarbonate solution
  7. stirringThe mixture was stirred at room temperature for 1 h
  8. filtrationfiltered
  9. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-762593b1ea50489893651c27fc86d6ec
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721259

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