Ethanolamine → HCID 58901741, compound

HRID 1853928Notes

Reaction equation

HRID 1853928 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])=[C:15]([F:23])[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:20])=[O:21])=[C:15]([F:23])[CH:14]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 58901741HCID 58901741, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminoethanol (0.24 mL, 4.0 mmol), and triethylamine (1.5 mL, 11 mmol) in anhydrous THF (15 mL) was added 4-bromo-2-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.7 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 (850 mg, 77%): ESI MS m/z 298 [C8H9BrFNO3S+H]+.

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-2f8e2df20e734353a0ca330433f81a34
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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