Aniline → Benzenesulfonanilide

HRID 2422823Notes

Reaction equation

HRID 2422823 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([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:2]1([NH:1][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7369Benzenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 74296BenzenesulfonanilideYield 68%

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 benzene sulfonyl chloride (0.95 g, 5.36 mmol) for 10 min at rt. Then reaction mixture was stirred with water at 60° C. for 30 minutes, filtered, washed with water and dried to gave 17 (0.85 g, 68%). Product was purified by FCC by using eluent as in 15 to give 17 as white flakes (0.79 g), mp: 107-109° C. (lit33A 110° C.); IR (CHCl3) 3256, 1599, 1331, 1162, cm−1; 1H NMR (500 MHz, DMSOD6) δ 6.4 (br, 1H, NH), and 7.04-7.77 (m, 10H, aromatic). HRMS calcd 256.04027 (C12H11NO2S.Na+), found 256.04016.

Workup

  1. customThe title compound was synthesized
  2. customThen reaction mixture
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-abdbb7ab6a894f07b2e47e8502120a44
Source dataset
uspto-grants-2011_06
Patent number
US07960435B2

Reaction notes

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