Pyridine → 4-nitro-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide

HRID 1049044Notes

Reaction equation

HRID 1049044 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].N1C=CC=CC=1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(Cl)Cl>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:2]([F:10])([F:11])[F:1])(=[O:29])=[O:28])=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69222-(Trifluoromethyl)anilineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 23029924-nitro-N-[2-(trifluoromethyl)phenyl]benzenesulfonamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(trifluoromethyl)aniline (1.51 g, 9.37 mmol) and pyridine (1.08 mL, 13.38 mmol) in DCM (30 mL) was treated with 4-nitrobenzenesulfonyl chloride (1.48 g, 6.69 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 M aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-nitro-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (1.91 g, 82%). 1H NMR (300 MHz, CDCl3) δ 8.31-8.23 (m, 2H), 7.95-7.85 (m, 3H), 7.64-7.50 (m, 2H), 7.31 (t, J=7.7 Hz, 1H), 6.89 (br s, 1H). LCMS (m/z, Method A) ES+ 347.1 [M+1]+.

Workup

  1. washwashed with 1 M aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c28687d214b34866b639bcd4c04bd1af
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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