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

HRID 1957370Notes

Reaction equation

HRID 1957370 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-b0fc1af8f4fb4187a044008c4a1a69e0
Source dataset
uspto-grants-1998_07
Patent number
US05783704

Reaction notes

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