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

HRID 1615018Notes

Reaction equation

HRID 1615018 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C([O-])([O-])=O.[Na+].[Na+].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21])([O-:13])=[O:12].C(Cl)Cl>C(OCC)(=O)C.O>[OH:2][CH2:1][CH2:3][NH:4][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N+:11]([O-:13])=[O:12])(=[O:21])=[O:22]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 3102011N-(2-hydroxyethyl)-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Ethanolamine (10 mL, 165 mmol) was dissolved in ethyl acetate (60 mL). Then a solution of Na2CO3 (22.7 g, 214.2 mmol) in water (100 mL) was added. Then, a solution of 2-nitrobenzenesulfonyl chloride (35.0 g, 157.9 mmol) in ethyl acetate (100 mL) was added dropwise under stirring. The resulting solution was stirred at room temperature for 2 h (TLC monitoring, eluent: CH2Cl2). The organic layer was separated, washed with water and a solution of citric acid, dried over Na2SO4, and evaporated. Yield of 54: 29.5 g (73%) as white crystals.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala solution of citric acid, dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-ccaa7e150ede455d88d2205d5535cac7
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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