Ethanolamine → 4-Bromo-N-(2-hydroxyethyl)benzene-1-sulfonamide

HRID 1853929Notes

Reaction equation

HRID 1853929 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH2:2][CH2:3][OH:4])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 4585694-Bromo-N-(2-hydroxyethyl)benzene-1-sulfonamideYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminoethanol (2.3 mL, 39 mmol), and triethylamine (16 mL, 120 mmol) in anhydrous THF (100 mL) was added 4-bromobenzene-1-sulfonyl chloride (10 g, 39 mmol) portion wise and the reaction mixture stirred at room temperature for 16 h. The reaction was filtered, the filtrate was concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (5.5 g, 50%): 1H NMR (500 MHz, CDCl3) δ 7.74 (td, J=9.0, 2.1 Hz, 2H), 7.67 (td, J=9.0, 2.1 Hz, 2H), 5.08 (s, 1H), 3.72 (t, J=5.1 Hz, 2H), 3.12 (t, J=4.8 Hz, 2H), 1.83 (s, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-dc5eee79b5aa4385b9c33f69f38fd460
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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