Methanol → 2-Aminothiophene-3-carboxamide

HRID 269854

Reaktionsgleichung

Reaktionsgleichung von HRID 269854
O[CH:2]1[CH2:7]SC(O)C[S:3]1.[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].CO>O.C(N(CC)CC)C>[NH2:10][C:9]1[S:3][CH:2]=[CH:7][C:11]=1[C:12]([NH2:14])=[O:13]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 7898CyanoacetamideHCID 983301,4-Dithiane-2,5-diol

Produkt 1

HCID 6994952-Aminothiophene-3-carboxamideAusbeute 141,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
37.5 °C

Versuchsvorschrift

2,5-Dihydroxy-1,4-dithiane (76 g) and cyanoacetamide (84 g) were added to a mixture of methanol (180 mL), water (10 mL) and triethylamine (10 g). The resulting mixture was heated at 35-40° C. for about 30 minutes while stirring, and then heated to 50-60° C. for an additional 30 minutes with stirring. The reaction mixture was then cooled to room temperature and poured into a mixture of ice (100 g)/water (360 mL). A fine precipitate formed upon addition, which was filtered and dried overnight to give 100.6 g of the title compound as a pale gray powder ((M+H)+=143, M.P.=159.0-159.6° C.).

Aufarbeitung

  1. temperatureheated to 50-60° C. for an additional 30 minutes
  2. stirringwith stirring
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customA fine precipitate formed upon addition, which
  5. filtrationwas filtered
  6. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-935fc3f083c445918b8be8fdace31fac
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449472B2

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