Hydrazine → HCID 71258144, compound

HRID 1777066Notes

Reaction equation

HRID 1777066 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14](OC)=[O:15])(=[O:10])=[O:9])[CH2:4][CH2:3]1.[NH2:21][NH2:22]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([NH:21][NH2:22])=[O:15])(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 31699716HCID 31699716, compound

Product 1

HCID 71258144HCID 71258144, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-((4-methylpiperazin-1-yl)sulfonyl)benzoate (200 mg, 0.670 mmol) was added to the hydrazine (43.0 mg, 1.341 mmol) in methanol and refluxed for 8 h at 65° C. Following cooling, reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by flash chromatography (3% methanol/DCM) to yield the 3-((4-methylpiperazin-1-yl)sulfonyl)benzohydrazide (125 mg, 0.406 mmol, 60.6% yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.08 (s, 1H), 8.12 (m, 2H), 7.84 (d, 1H, J=7.6 Hz), 7.72 (t, 1H, J=7.6 Hz), 4.57 (m, 1H), 2.88 (m, 4H), 2.32 (m, 4H), 2.10 (s, 3H). Mass [M+H]+: 298.9

Workup

  1. temperatureFollowing cooling
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customcompound was purified by flash chromatography (3% methanol/DCM)

Sources & evidence

ORD record
ord-c1ec12eb26294f02b279737df3c26afc
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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