Hydrazinecarboxylic acid, ethyl ester → Ethyl 2-carbamothioylhydrazine-1-carboxylate

Reaction equation

[N-:1]=[C:2]=[S:3].[C:4]([O:8][CH2:9][CH3:10])(=[O:7])[NH:5][NH2:6]>>[C:4]([NH:5][NH:6][C:2]([NH2:1])=[S:3])([O:8][CH2:9][CH3:10])=[O:7]

Participants

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl ester

HCID 178418790HCID 178418790, compound

Product 1

HCID 4085798Ethyl 2-carbamothioylhydrazine-1-carboxylate

Procedure

For the synthesis of compounds of formula (I) wherein E=--S--, Reaction Schemes 13 and 14 may be utilized. In Reaction Scheme 13, the isothiocyanate 22 is reacted with ethyl carbazate (8) to give the 1-(carbethoxy)thiosemicarbazide 48. By standard conditions, 48 is S-alkylated to yield 49, which can be cyclized to the triazolinone 50 by heating, optionally in the presence of base or acid [F. Kurzer and D. R. Hanks, Chem. Ind. (London), 1143 (1966)]. Finally, alkylation of the triazolinone as in Reaction Scheme 1 provides the fully substituted product 51. ##STR58##

Workup

customIn Reaction Scheme 13

Sources & evidence

ORD record: ord-0e7ed9baa5544c5395cba2dee7b27e7a
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411980

Reaction notes

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