p-Toluidine → 4-Fluoro-N-(4-methylphenyl)benzenesulfonamide

HRID 971312Notes

Reaction equation

HRID 971312 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 7110724-Fluoro-N-(4-methylphenyl)benzenesulfonamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Toluidine (6.430 g, 60 mmol) was dissolved in pyridine (200 mL). The resulting mixture was cooled down to 0° C. 4-fluoro-benzenesulfonyl chloride (7.784 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-methylphenyl)benzenesulfonamide (9.4754 g, 89%), was obtained as a colorless solid, in 98% 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-8912cf9b3f604e29935083c8d18147d1
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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