4-Methoxybenzenesulfonyl chloride → 4-Methoxybenzenesulfonamide

HRID 1860517Notes

Reaction equation

HRID 1860517 reaction equation
C1(C)C=CC([N:7]2C(N)=CC(C3C=CC(N)=CC=3)=N2)=CC=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:7])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 786192HCID 786192, compound

Product 1

HCID 707894-Methoxybenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-tolyl)-3-(4-aminophenyl)-5-aminopyrazole (0.6 g, 2.27 mmol) in THF (20 mL) and H2O (8 mL) at room temperature was added 4-methoxybenzenesulfonyl chloride (0.94 g, 4.55 mmol) and potassium carbonate (0.95 g, 6.88 mmol). The mixture was stirred at room temperature overnight and was then partitioned between H2O (20 mL) and EtOAc (100 mL). The layers were separated and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparatory TLC, eluting with 2:1 hexanes/EtOAc to yield N-[4-5-amino-1-(4-methylphenyl)-1H-pyrazol-3-yl]phenyl]-4-methoxy benzenesulfonamide.

Workup

  1. customwas then partitioned between H2O (20 mL) and EtOAc (100 mL)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparatory TLC
  6. washeluting with 2:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-f664ed63dc0d4812a18f1a3ae8a5fa60
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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