4-Chloroaniline → N-(4-Chlorophenyl)-4-fluorobenzenesulfonamide

HRID 971315Notes

Reaction equation

HRID 971315 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 341407N-(4-Chlorophenyl)-4-fluorobenzenesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloroaniline (6.697 g, 52 mmol) was dissolved in pyridine (250 mL). The resulting mixture was cooled down to 0° C. 4-fluoro-benzenesulfonyl chloride (7.775 g, 40 mmol) was added in portions. The mixture was stirred between 0° C. and room temperature overnight. Solvents were evaporated to dryness. The crude oil was dissolved in ethyl acetate (150 mL) and washed with 10% HCl (2×75 mL) and brine (1×75 mL). Organic phase was dried over magnesium sulfate before filtering and removal of solvent. The resulting solid was recrystallized in cyclohexane/ethyl acetate 9:1. The desired product, e.g. 4-fluoro-N-(4-chlorophenyl)benzenesulfonamide (6.630 g, 58%), was obtained as a colorless solid, in 97.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customSolvents were evaporated to dryness
  2. dissolutionThe crude oil was dissolved in ethyl acetate (150 mL)
  3. washwashed with 10% HCl (2×75 mL) and brine (1×75 mL)
  4. dry with materialOrganic phase was dried over magnesium sulfate
  5. filtrationbefore filtering
  6. customremoval of solvent
  7. customThe resulting solid was recrystallized in cyclohexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-f396663401d6401e9f317f5031fbc68e
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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