Triethylamine → N-(2-iodophenyl)methanesulfonamide

HRID 985728Notes

Reaction equation

HRID 985728 reaction equation
[I:1][C:2]1[CH:8]=[C:7](Cl)[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:18]([CH3:17])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 780001N-(2-iodophenyl)methanesulfonamideYield 111.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of the 2-iodo-4-chloroaniline (5.0 g, 20 mmol) and triethylamine (8.3 mL, 60 mmol) in methylene chloride (200 mL), the solution of methanesulfonyl chloride (3.4 mL, 44 mmol) was added slowly. The solution then was stirred at room temperature for 2 h. After being washed by HCl solution (0.5 N, 2×100 mL), NaOH solution (0.5 N, 2×100 mL), brine (100 mL), the organic layer was dried over Na2SO4 and concentrated providing the title compound (6.6 g).

Workup

  1. washAfter being washed by HCl solution (0.5 N, 2×100 mL), NaOH solution (0.5 N, 2×100 mL), brine (100 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4dcb3a2d8e34a1780f1edc9a4bc0fa2
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

Loading…