Hydrazine hydrate (1:1) → HCID 22272487, compound

HRID 2237655Notes

Reaction equation

HRID 2237655 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:24]([O-])=O)=[C:12]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=2)[CH2:4][CH2:3]1.O.NN.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([S:40]([Cl:43])(=[O:42])=[O:41])[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]>C1COCC1.[Ni]>[ClH:43].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([S:40]([NH:24][C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:13][C:12]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=[O:41])=[O:42])[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 11164762N-[5-(4-methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamide

Product 1

HCID 22272487HCID 22272487, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-[5-(4-Methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamide (0.600 g, 1.59 mmol) was dissolved in THF (20 mL) followed by the addition of Raney-Ni (0.322 g, in ethanol) and hydrazine hydrate (0.100 g, 2.0 mmol). The reaction mixture was stirred for 1 h, filtered through Celite and concentrated. The residue was dissolved in pyridine (12 mL) and divided in 12 equal parts. To one part was added 3,4-dimethoxy-benzenesulfonylchloride (47 mg, 0.20 mmol). The reaction mixture was stirred overnight, poured into petroleum ether to form a precipitate that was collected by centrifugation. The precipitate was purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5 to 9:1). The pure product was dissolved in MeOH and treated with HCl/diethyl ether to give 34.5 mg, (45% yield). MS (posES-FIA) m/z=found: 547.4; Calcd: 546.16.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in pyridine (12 mL)
  4. stirringThe reaction mixture was stirred overnight
  5. customto form a precipitate that
  6. customwas collected by centrifugation
  7. customThe precipitate was purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5 to 9:1)
  8. dissolutionThe pure product was dissolved in MeOH
  9. additiontreated with HCl/diethyl ether
  10. customto give 34.5 mg, (45% yield)

Sources & evidence

ORD record
ord-12f6c1e4d86b4712b12767d66fefa4da
Source dataset
uspto-grants-2010_05
Patent number
US07718650B2

Reaction notes

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