Ethanolamine → N-(2-hydroxyethyl)benzenesulfonamide

HRID 1934637Notes

Reaction equation

HRID 1934637 reaction equation
[CH2:1]([NH2:4])[CH2:2][OH:3].[C:5]1([S:11](Cl)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>O>[OH:3][CH2:2][CH2:1][NH:4][S:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 7369Benzenesulfonyl chloride2×HCID 14798Sodium Hydroxide

Product 1

HCID 1722145N-(2-hydroxyethyl)benzenesulfonamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

128.3 g of 2-ethanolamine (2.1 mol) and 150 g of water are introduced into a 1 litre reactor equipped with a thermostatically-controlled jacket, a stirrer and a dropping funnel. 353 g of benzenesulphonyl chloride (2 mol) are introduced into the dropping funnel. The reactor is heated to approximately 60° C. and the benzenesulphonyl chloride is then allowed to run dropwise into the reactor at the rate of approximately 3 ml/min. The exothermicity of the reaction is thus controlled and the temperature changes to reach 70 to 75° C. at the end of addition. The pH is prevented from falling below 9 by gradual addition of a 20% solution of sodium hydroxide in water. After a few hours, the reaction is complete. The reaction mixture is then extracted with a third water-insoluble solvent, such as ethyl acetate. This organic phase is collected. The aqueous phase is extracted and the combined organic phases are distilled under vacuum in order to remove the extraction solvent. 384 g of N-(2-hydroxyethyl)benzenesulphonamide are thus obtained, i.e. a yield of 95.5% with a purity of greater than 99%. This product, which is liquid at room temperature, is characterized by IR spectroscopy and NMR spectro-scopy, as well as by GC and HPLC analysis.

Workup

  1. customequipped with a thermostatically-controlled jacket, a stirrer and a dropping funnel
  2. additionthe temperature changes to reach 70 to 75° C. at the end of addition
  3. waitAfter a few hours
  4. extractionThe reaction mixture is then extracted with a third water-insoluble solvent, such as ethyl acetate
  5. customThis organic phase is collected
  6. extractionThe aqueous phase is extracted
  7. distillationthe combined organic phases are distilled under vacuum in order
  8. customto remove the extraction solvent

Sources & evidence

ORD record
ord-4934e9f7261f4d2ebc281f0a258c9482
Source dataset
uspto-grants-2002_05
Patent number
US06384115B1

Reaction notes

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