Aniline → Benzenesulfonamide, 4-methyl-N-phenyl-

HRID 2395925

Reaction equation

HRID 2395925 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl.CCOCC>[C:2]1([NH:1][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21226206Ethyl acetate hexane

Product 1

HCID 2456Benzenesulfonamide, 4-methyl-N-phenyl-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Aniline (1.86 g, 0.02 mol) was dissolved in methylene chloride under nitrogen and triethylamine (3.8 mL, 0.02 mol) was added. This solution wascooled in an ice bath and a solution of p-toluenesulfonyl chloride (3.8 g, 0.02 mol) was added dropwise via a syringe. After stirring this solution for 4 h at room temperature, TLC analysis (silica gel, 20% ethyl acetate/hexane) indicated completion of the reaction. The reaction mixturewas poured into ether and the precipitate filtered. The ether layer was washed with water, dried over MgSO4 and concentrated to yield an oilymaterial. This crude product was chromatographed on silica using 35% ethyl acetate and hexane to obtain a solid which was further recrystallized in methylene chloride/hexane; m.p. 104° C.; 1H NMR (CDCl3) δ2.36 (s, 3H), 7.07-7.25 (m, 8H), 7.67-7.69 (d, 2H).

Workup

  1. customThis solution wascooled in an ice bath
  2. customcompletion of the reaction
  3. filtrationthe precipitate filtered
  4. washThe ether layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto yield an oilymaterial
  8. customThis crude product was chromatographed on silica using 35% ethyl acetate and hexane
  9. customto obtain a solid which
  10. customwas further recrystallized in methylene chloride/hexane

Sources & evidence

ORD record
ord-c252f627c2fd4c92ac36b2911bd08852
Source dataset
uspto-grants-1996_02
Patent number
US05491072

Linked notes

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