Sodium Hydroxide → N-[5-(4-methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamide

HRID 230476Notes

Reaction equation

HRID 230476 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[OH-].[Na+]>>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:11])=[O:10])[CH:7]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 22272573HCID 22272573, compound

Product 1

HCID 11164762N-[5-(4-methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamideYield 78%

Procedure

N-(5-fluoro-2-nitrophenyl)benzenesulfonamide (2×0.50 g, 1.688 mmol) was treated with N-methyl-piperazine (2×4.65 g, 45.6 mmol) and put in two pyrex tubes and sealed. Each tube was put in a LabWell MW-10 microwave oven for 2 min at 50 W. The reaction mixtures were combined and poured into 0.5 M NaOH (aq) and extracted with CH2Cl2, dried (MgSO4) and concentrated to give 0.99 g, (2.63 mmol) in 78% yield as a yellow solid. Anal (C17H20O N4 O4 S)C, H, N, S; MS (posES-FIA) m/z=found: 377.4; Calcd: 376.12.

Workup

  1. customsealed
  2. customThe reaction mixtures
  3. extractionextracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give 0.99 g, (2.63 mmol) in 78% yield as a yellow solid

Sources & evidence

ORD record
ord-5167705b4dc247be958bd5867fcd75fb
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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