Diethanolamine → HCID 15683605, compound

HRID 1458713Notes

Reaction equation

HRID 1458713 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[CH3:8][N:9]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1Cl)[CH3:10]>CS(C)=O>[CH3:10][N:9]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4])[CH3:8]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 881114HCID 881114, compound

Product 1

HCID 15683605HCID 15683605, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

Diethanolamine (5 g; 48.6 mmol) was added to a solution of 5 g (18.4 mmol) of N-[(N,N-dimethylamino)ethyl]-2-chloro-5-nitrobenzamide in 10 ml of DMSO, followed by stirring at 150° C. for 3.5 hours. After the resulting mixture was cooled to room temperature, it was extracted with ethyl acetate. Magnesium sulfate was added to the extract to dry the same, and the solvent was then distilled out under reduced pressure. The residue was purified by chromatography on a silica gel column (ethyl acetate/methanol=1/0→1/1), whereby 2.6 g of the title compound were obtained as a colorless oil (yield: 38%).

Workup

  1. temperatureAfter the resulting mixture was cooled to room temperature
  2. extractionit was extracted with ethyl acetate
  3. additionMagnesium sulfate was added to the
  4. extractionextract
  5. customto dry the same, and the solvent
  6. distillationwas then distilled out under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column (ethyl acetate/methanol=1/0→1/1)

Sources & evidence

ORD record
ord-77b44e02df984a72a19da30cd9eafae6
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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