Réaction #55397

ord-dcbc79e18d474118a2d91bc9adf16d18

Équation de réaction

NNC(N)=S
thiosemicarbazide
COCC(=O)O
methoxyacetic acid
COCc1nnc(N)s1
5-amino-2-methoxymethyl-(1,3,4)-thiadiazole

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

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°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04220652uspto-grants-1980_09