Water → HCID 23317121, compound

HRID 1982617Notes

Reaction equation

HRID 1982617 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4](=O)[CH:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:6])[CH3:2].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:3]([CH2:4][CH:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:6])[CH2:17][CH3:18])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 23317113HCID 23317113, compound

Product 1

HCID 23317121HCID 23317121, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.31 g of N,N-diethyl 2-(3,4-dichloroanilino)propionamide were dissolved in 15 ml of dry tetrahydrofuran. This solution was added dropwise in 5 minutes to a stirred suspension of 0.61 g of lithium-aluminium-hydride in 25 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 6 hours and was left to stand overnight. The next day 0.6 ml of water, 1.5 ml of 15% sodium hydroxide solution and 1.5 ml of water were added successively. After filtration the organic layer was washed with water, dried and filtered. After evaporating the solvent, 2.06 g of the desired product were obtained; identification by means of thin-layer chromatography. The product was purified by means of columnchromatography (acetone as an eluent), after which 1.41 g or an orange oil was obtained; nD25 =1.5404.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. waitwas left
  3. filtrationAfter filtration the organic layer
  4. washwas washed with water
  5. customdried
  6. filtrationfiltered
  7. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-f35be616a8094ce788d818383781d330
Source dataset
uspto-grants-1986_06
Patent number
US04596891

Reaction notes

Loading…