Hydrazine hydrate (1:1) → 4-Methylpiperazine-1-carbothiohydrazide

HRID 1258112Notes

Reaction equation

HRID 1258112 reaction equation
O.[NH2:2]N.[N:4]1([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[S:10])C=CN=C1>C(O)C>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:9](=[S:10])[NH:4][NH2:2])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59761525Imidazol-1-yl-(4-methyl-piperazin-1-yl)-methanethione

Product 1

HCID 152917424-Methylpiperazine-1-carbothiohydrazideYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-methylpiperazine-1-carbothiohydrazide (intermediate 6) can be formed according to the following scheme. Hydrazine hydrate (MW 50.06, 0.26 ml, 5.44 mmol, 1.1 eq) was added to a solution of imidazol-1-yl-(4-methyl-piperazin-1-yl)-methanethione (3; MW 210.30, 1.040 g, 4.95 mmol, 1 eq) in 30 ml ethanol at room temperature. The reaction mixture was stirred under reflux for 2 hours. This organic solution was concentrated. The solid thus obtained was triturated with diethyl ether and filtered to yield 4-methylpiperazine-1-carbothiohydrazide (6; MW 174.27, 0.53 g, 3.04 mmol, 61% yield) as a white solid which was used without further purification. TLC (CH2Cl2/MeOH: 90/10): Rf=0.15, Product UV and Ninhydrin stain active. 1H-NMR (400 MHz, DMSO-d6), δ ppm: 2.17 (s, 3H), 2.28 (t, 4H, J=5 Hz), 3.69 (t, 4H, J=5 Hz).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThis organic solution was concentrated
  3. customThe solid thus obtained
  4. customwas triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9d9a890ecf85425b80f61cf71ebfbac7
Source dataset
uspto-grants-2013_06
Patent number
US08466151B2

Reaction notes

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