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

HRID 2422822Notes

Reaction equation

HRID 2422822 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>O>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2456Benzenesulfonamide, 4-methyl-N-phenyl-Yield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was synthesized by triturating aniline (0.5 g, 5.36 mmol), powdered sodium bicarbonate (0.9 g, 1.07 mmol) and powdered p-toluene sulfonyl chloride (1.02 g, 5.36 mmol) for 5 min at rt. The reaction mixture was stirred with water, filtered, washed with water and dried to give 16 (1.13 g, 84.9%). Product was purified by FCC by using eluent as in 15 to give 16 as white powder (0.9 g), mp-95-97° C. (lit32A 96° C.); IR(CHCl3) 3255, 1599, 1342, 1160, cm−1; 1H NMR (500 MHz, DMSOD6) δ 2.37 (s, 3H, CH3), 6.53 (br, 1H, NH), and 7.04-7.65 (m, 9H, aromatic). HRMS calcd 270.05592 (C13H13NO2S.Na+), found 270.05589.

Workup

  1. customThe title compound was synthesized
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-40821b1243f541408d03abb1df746225
Source dataset
uspto-grants-2011_06
Patent number
US07960435B2

Reaction notes

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