Ethanolamine → HCID 2055080, compound

HRID 352389Notes

Reaction equation

HRID 352389 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1.O>[OH:2][CH2:1][CH2:3][NH:4][S:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 2055080HCID 2055080, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.5 mL (3.54 g, 58 mmol) of ethanolamine in 20 mL of THF and 5 mL of water, was added 10.7 mL of triethylamine. After cooling in an ice bath, 10.53 g (51 mmol) of para-methoxybenzenesulfonyl chloride was slowly added over ten minutes. After stirring at room temperature for 1 hour, the solvent was removed under reduced pressure and ethyl acetate and water added. The organic layer was separated, washed with 5% KHSO4 and brine, dried over sodium sulfate, filtered and stripped to afford 10.3 g of the desired N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide, m/e=238 (M+Li).

Workup

  1. temperatureAfter cooling in an ice bath
  2. customthe solvent was removed under reduced pressure and ethyl acetate and water
  3. additionadded
  4. customThe organic layer was separated
  5. washwashed with 5% KHSO4 and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-76e2e8d3b839448d910b713ab20da7e4
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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