Potassium Carbonate → N-[2-(2-hydroxyethoxy)ethyl]-1-(2-nitrophenyl)methanesulfonamide

HRID 1259037Notes

Reaction equation

HRID 1259037 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].C(=O)([O-])[O-].[K+].[K+].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][S:24](Cl)(=[O:26])=[O:25])([O-:16])=[O:15]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][S:24]([CH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15])(=[O:25])=[O:26]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 13578DiglycolamineHCID 4305447(2-nitrophenyl)methanesulfonyl Chloride

Product 1

HCID 62498280N-[2-(2-hydroxyethoxy)ethyl]-1-(2-nitrophenyl)methanesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(2-aminoethoxy)ethanol (0.557 g), 5.31 mmol) and potassium carbonate (1.17 g, 8.48 mmol) in toluene (50 ml) and water (4 ml) at room temperature, was added 2-nitro-alpha-toluenesulfonyl chloride (1.00 g, 4.24 mmol) in one portion and the reaction was left to stir overnight. The reaction was diluted with ethyl acetate and water. The organic layer was separated before being washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The crude material was purified by column chromatography eluting with ethyl acetate:hexane to afford N-[2-(2-hydroxyethoxy)ethyl]-1-(2-nitrophenyl)methanesulfonamide as product (0.155 g, 12%); Rf (ethyl acetate:hexane 2:1) 0.11; δH (400 MHz, CDCl3) 8.02 (1H, d), 7.67 (2H, m), 7.53 (1H, dt), 5.15 (1H, brs), 4.86 (2H, s), 3.71 (2H, s), 3.56 (4H, m), 3.19 (2H, m) and 2.36 (1H, s); LCMS Rt=2.60 min, m/z (APCI) 305 (MH+).

Workup

  1. waitthe reaction was left
  2. customThe organic layer was separated
  3. washbefore being washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe crude material was purified by column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-897a16964175450fa14172374b7b92f5
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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