Hydrazine hydrate (1:1) → HCID 86232178, compound

HRID 2074125Notes

Reaction equation

HRID 2074125 reaction equation
O.[NH2:2]N.[N:4]1([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:18])[CH2:13][CH2:12]2)=[S:10])C=CN=C1>C(O)C>[F:26][C:25]([F:28])([F:27])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9]([NH:4][NH2:2])=[S:10])[CH2:12][CH2:13]1)=[O:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86620010HCID 86620010, compound

Product 1

HCID 86232178HCID 86232178, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of hydrazine hydrate (0.584 mL, 12.03 mmol) and [4-(imidazole-1-carbothioyl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (4.03 g, 10.94 mmol) in anhydrous ethanol was refluxed for 3 hours. The reaction mixture was cooled to room temperature and kept in the fridge overnight. The precipitate formed was collected by filtration and washed with ethanol, dried in vacuo to yield 4-(2-trifluoromethylbenzoyl)piperazine-1-carbothioic acid hydrazide in 60% yield (2.20 g). 1H NMR (500 MHz, CDCl3) δ 7.72 (d, J=7.8 Hz, 1H), 7.62 (dd, J=7.5, 7.5 Hz, 1H), 7.55 (dd, J=7.5, 7.5 Hz 1H), 7.33 (d, J=7.5 Hz, 1H), 3.70-4.00 (m, 8H). MS (ES+) m/z 333 (M+1).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customkept in the fridge overnight
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1a8beaeef5cc459c9db00936be3fa88d
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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