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

HRID 2276936Notes

Reaction equation

HRID 2276936 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 1N 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 1N 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-f3691eda11bd41ff98e41dd4645d098d
Source dataset
uspto-grants-2015_09
Patent number
US09133145B2

Reaction notes

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