Diethanolamine → N,N-Bis-(2-hydroxy-ethyl)-2-nitrobenzenesulfonamide

HRID 1961677Notes

Reaction equation

HRID 1961677 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH:14]([CH2:18][CH2:19][OH:20])[CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[OH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][OH:20])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 60723400N,N-Bis-(2-hydroxy-ethyl)-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-nitrobenzenesulfonyl chloride (10.5 g, 47.6 mmol) in anhydrous methylene chloride (25 mL) was added dropwise with stirring to a 0° C. solution of diethanolamine (5.00 g, 47.6 mmol) and triethylamine (4.92 g, 47.6 mmol) in anhydrous methylene chloride (50 mL). Reaction stirred three hours at 0° C. and then overnight at room temperature. Reaction mixture concentrated under reduced pressure. Residue dissolved in ethyl acetate, washed with 1 N NaOH, saturated NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with ethyl acetate to afford the title compound. MS (ESI) m/z 291 (M+H)+.

Workup

  1. customReaction
  2. customovernight
  3. customat room temperature
  4. customReaction mixture
  5. concentrationconcentrated under reduced pressure
  6. dissolutionResidue dissolved in ethyl acetate
  7. washwashed with 1 N NaOH, saturated NaHCO3, and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-2accc6e5623046c58806e5dfa5c7cd12
Source dataset
uspto-grants-2013_04
Patent number
US08415354B2

Reaction notes

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