Ethanol → Methyl 4-morpholinethiocarboximidate hydroiodide

HRID 128068

Reaktionsgleichung

Reaktionsgleichung von HRID 128068
[N:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[I:10]C.[CH2:12](O)C>CCOCC>[IH:10].[N:1]1([C:7]([S:9][CH3:12])=[NH:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 6328Methyl iodideHCID 23935444-Morpholinecarbothioamide

Produkt 1

HCID 16333240Methyl 4-morpholinethiocarboximidate hydroiodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4.65 g. of 4-morpholinethiocarboxamide [W. G. Finnegan, et al., J. Org. Chem. 18, 779 (1952)] and 4.54 g. of iodomethane in 50 ml. of ethanol is allowed to stand 48 hours at room temperature, then diluted with 250 ml. of ether to give a colorless crystalline precipitate of methyl 4-morpholinethiocarboximidate hydroiodide. A solution of 5.76 g. of this product and 1.1 g. of hydrazine hydrate in ethanol is heated under reflux for about 2 hours and then treated with 2.1 g. of 9,10-anthracenedicarboxaldehyde in 200 ml. of ethanol and 2 ml. of glacial acetic acid by heating under reflux for 3.5 hours. The solution is filtered and then evaporated to give an orange solid which is recrystallized from ethanol-ether to give the title compound, m.p. 280° C.

Aufarbeitung

  1. additiondiluted with 250 ml

Quellen und Nachweise

ORD-Eintrag
ord-31a320262aa54209a4f7df096b27985a
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258181

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