Methoxyacetic Acid → 5-(Methoxymethyl)-1,3,4-thiadiazol-2-amine

HRID 262189

Reaktionsgleichung

Reaktionsgleichung von HRID 262189
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][O:7][CH2:8][C:9](O)=O>O>[NH2:5][C:3]1[S:4][C:9]([CH2:8][O:7][CH3:6])=[N:1][N:2]=1

Komponenten

4

Edukt 2

HCID 12251Methoxyacetic AcidHCID 2723789Thiosemicarbazide

Produkt 1

HCID 6608445-(Methoxymethyl)-1,3,4-thiadiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Addition of phosphonyl chloride to a mixture of thiosemicarbazide and methoxyacetic acid at 60°-95° and working up of the product yields 5-amino-2-methoxymethyl-(1,3,4)thiadiazole, m.p. 177°-179° (from water). When this compound is diazotised and treated with cuprous bromide 5-bromo-2-methoxymethyl-(1,3,4)-thiadiazole results and reaction of this bromo compound with zinc dust in acetic acid at room temperature yields 2-methoxymethyl-(1,3,4)-thiadiazole, m.p. 30.5°-32°.

Quellen und Nachweise

ORD-Eintrag
ord-bce5322235df483eaf874ea886e67157
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153704

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