Formaldehyde → 5-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride

HRID 1586712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586712
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[CH2:11]=O.[ClH:13].[CH3:14][NH:15][CH3:16]>C(O)(=O)C>[ClH:13].[CH3:14][N:15]([CH2:11][CH:8]1[CH2:7][S:6][C:5]2[S:1][CH:2]=[CH:3][C:4]=2[C:9]1=[O:10])[CH3:16]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 110302745,6-Dihydro-4H-thieno[2,3-b]thiopyran-4-one

Produkt 1

HCID 126753075-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochlorideAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5,6-dihydrothieno[2,3-b]thiopyran-4-one (12.5 g, 0.074 mol), paraformaldehyde (7.5 g, 0.25 mol), dimethylamine-hydrochloride (40 g, 0.49 mol) and acetic acid (2 ml) was heated with stirring at 100° C. for 1 hour. After allowing to cool to room temperature, the solid was triturated with ethanol and the solid was collected on a filter to yield 16.3 g (83%) of the title compound. An analytical sample was prepared by crystallization from 95% ethanol and filtration through a pad of norite-ducco-supercel to yield product with mp 155°-157° C. Anal. Calc'd. for C10H13NOS2.HCl.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto cool to room temperature
  3. customthe solid was triturated with ethanol
  4. customthe solid was collected on
  5. filtrationa filter

Quellen und Nachweise

ORD-Eintrag
ord-1b9973f655274e1f9adf7e037a0fe2a9
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05215989

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