Ethanolamine → N-(2-hydroxyethyl)-2-nitrobenzenesulfonamide

HRID 495206Notes

Reaction equation

HRID 495206 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14](Cl)(=[O:16])=[O:15])([O-:7])=[O:6].N1C=CC=CC=1.O>CN(C)C=O>[OH:4][CH2:3][CH2:2][NH:1][S:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N+:5]([O-:7])=[O:6])(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 3102011N-(2-hydroxyethyl)-2-nitrobenzenesulfonamideYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

2-Aminoethanol (4.0 mL, 66 mmol) was dissolved in N,N-dimethylformamide (50 mL). After the solution was cooled to −10° C., 2-nitrobenzenesulfonyl chloride (12 g, 52 mmol) and pyridine (4.7 mL, 58 mmol) were added dropwise thereto, followed by stirring for 50 minutes, while the temperature was raised to room temperature. To the reaction mixture was added water (0.20 L), and the mixture was extracted with ethyl acetate (0.10 L×6). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain N-(2-hydroxyethyl)-2-nitrobenzenesulfonamide (10 g, 62%).

Workup

  1. temperaturewas raised to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (0.10 L×6)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d4f1846d8f24ece99e7654a17270136
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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