Chlorine → 4-[5-(4Chlorophenyl)-4-chloro-1h-pyrazol-1-yl]benzenesulfonamide

HRID 1274293Notes

Reaction equation

HRID 1274293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:23]Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[CH:10][C:9]=2[Cl:23])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 108305124-[5(4-chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamide

Product 1

HCID 120828214-[5-(4Chlorophenyl)-4-chloro-1h-pyrazol-1-yl]benzenesulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-[5-(4-Chlorophenyl)-1H-pyrazol-1-yl]benzenesulfonamide from Step 2 (3.0 g, 9 mmol) was dissolved in 50 mL of acetic acid, and 9 mL of 1M chlorine in acetic acid was added dropwise. The mixture was stirred for 16 hours when sat. aq. sodium bicarbonate solution was slowly added until the mixture was neutral to pH paper. The mixture was extracted with ethyl acetate (3×50 mL), combined and washed with sat. aq. sodium bicarbonate and with brine, dried over magnesium sulfate, filtered, and concentrated. The resultant product was recrystallized from isopropanol to yield 2.6 g (78%) of a white solid: mp 168-171° C. (dec); 1H NMR (DMSO-D6 /300 MHz) 8.08 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.7 Hz, 2H), 7.46 (brs, 2H), 7.44 (d, J=8.7 Hz, 2H), 7.35 (d, J=8.7 Hz, 2H). Anal. Calc'd for C15H11N3SO2Cl2 : C, 48.93; H, 3.01; N, 11.41. Found: C, 49.01; H, 2.97; N, 11.41.

Workup

  1. additionwas slowly added until the mixture
  2. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  3. washwashed with sat. aq. sodium bicarbonate and with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-942b60d7374b4a07ba638f37c692c56a
Source dataset
uspto-grants-2000_12
Patent number
US06156781

Reaction notes

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