Diethanolamine → HCID 51396999, compound

HRID 231356Notes

Reaction equation

HRID 231356 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9]>O1CCCC1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[S:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 51396999HCID 51396999, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethanolamine (2.1 g, 20 mmol) in tetrahydrofuran (20 ml) was added slowly to a stirred solution of 3-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in tetrahydrofuran (80 ml) at 20°-25°. After stirring at this temperature for 3 days, solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. After drying the ethyl acetate extract (Na2SO4), filtering and concentrating, the residue was recrystallized from ethyl acetate-hexane to give 0.89 g of the sulfonamide, m.p. 100°-102° C.

Workup

  1. customsolvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialAfter drying the ethyl acetate
  4. extractionextract (Na2SO4)
  5. filtrationfiltering
  6. concentrationconcentrating
  7. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2ee52187e4634282b67ea29db3af8409
Source dataset
uspto-grants-1989_07
Patent number
US04845284

Reaction notes

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