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

HRID 894573

Reaction equation

HRID 894573 reaction equation
[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

Participants

4

Reactant 2

HCID 12251Methoxyacetic AcidHCID 2723789Thiosemicarbazide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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°.

Sources & evidence

ORD record
ord-8c26dff5f7bc496696e4daaa46a79d7e
Source dataset
uspto-grants-1981_08
Patent number
US04284640

Linked notes

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