Methylhydrazine → N-(5-Cyclobutyl-1,3,4-thiadiazol-2-yl)-1-methylhydrazine-1-carboxamide

HRID 1579488Notes

Reaction equation

HRID 1579488 reaction equation
[CH3:1][NH:2][NH2:3].[CH:4]1([C:8]2[S:12][C:11]([N:13]=[C:14]=[O:15])=[N:10][N:9]=2)[CH2:7][CH2:6][CH2:5]1.NN>C(Cl)Cl>[CH3:1][N:2]([C:14]([NH:13][C:11]1[S:12][C:8]([CH:4]2[CH2:5][CH2:6][CH2:7]2)=[N:9][N:10]=1)=[O:15])[NH2:3]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 9321HydrazineHCID 543457415-Cyclobutyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 21454645N-(5-Cyclobutyl-1,3,4-thiadiazol-2-yl)-1-methylhydrazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methylhydrazine (0.3 mole) in methylene chloride (150 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 5-Cyclobutyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.1 mole) is then added, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 4 hours. After this time the reaction mixture is stripped of solvent and excess hydrazine to yield the desired product 2-methyl-4-(5-cyclobutyl-1,3,4-thiadiazol-2-yl)semicarbazide.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperatureis heated
  5. temperatureat reflux for a period of about 4 hours

Sources & evidence

ORD record
ord-6fb54ecde6ef4bb9b536c047bdfd6033
Source dataset
uspto-grants-1976_01
Patent number
US03931209

Reaction notes

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