Methyl carbazate → N'-[2-(5-Methoxy-2-oxo-[1,3,4]thiadiazol-3-yl)-1-methyl-ethylidene]-hydrazinecarboxylic acid methyl ester

HRID 1636321Notes

Reaction equation

HRID 1636321 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[NH:2][NH2:3].[CH3:7][O:8][C:9]1[S:13][C:12](=[O:14])[N:11]([CH2:15][C:16](=O)[CH3:17])[N:10]=1>CO>[CH3:6][O:5][C:1]([NH:2][N:3]=[C:16]([CH3:17])[CH2:15][N:11]1[N:10]=[C:9]([O:8][CH3:7])[S:13][C:12]1=[O:14])=[O:4]

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 193507245-Methoxy-3-(2-oxopropyl)-3H-[1,3,4]thiadiazol-2-one

Product 1

HCID 53777430N'-[2-(5-Methoxy-2-oxo-[1,3,4]thiadiazol-3-yl)-1-methyl-ethylidene]-hydrazinecarboxylic acid methyl esterYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.1 g of methyl carbazate are added to a solution of 18.8 g of 5-methoxy-3-(2-oxo-propyl)-3H-[1,3,4]thiadiazol-2-one (Comp. 7.001) in 150 ml of methanol and the mixture is then stirred at room temperature for 36 hours. The reaction mixture is concentrated by evaporation and the residue is stirred with isopropanol and filtered with suction to yield 20.5 g of crystals of the title compound having a melting point of 142-143°.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. stirringthe residue is stirred with isopropanol
  3. filtrationfiltered with suction

Sources & evidence

ORD record
ord-9df8c800a475489eb424b4b5501d52a7
Source dataset
uspto-grants-2000_03
Patent number
US06034083

Reaction notes

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