Benzenesulfonyl chloride → N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)

HRID 400587

Reaction equation

HRID 400587 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N([CH2:25][CH3:26])CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[C:10]1([S:16]([N:6]([S:16]([C:26]2[CH:25]=[CH:12][CH:11]=[CH:10][CH:15]=2)(=[O:18])=[O:17])[C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=2[I:9])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 8239344-Bromo-2-iodoaniline

Product 1

HCID 60026850N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)Yield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-bromo-2-iodoaniline (8.5 g, 28.5 mmol) in 200 mL of dichloromethane was sequentially treated with benzenesulfonyl chloride (15 mL, 117.5 mmol) and triethylamine (25 mL, 179.6 mmol). After 4 days, the mixture was diluted with 100 mL of saturated aqueous sodium bicarbonate solution and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with 50 mL of brine, three 60 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether to afford 5.74 g (35% yield) of N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline).

Workup

  1. extractionextracted with three 100 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with 50 mL of brine, three 60 mL portions of saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-53ca051e0a414058a5925be0c353bd28
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Linked notes

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