Diethylaminoethyl chloride → HCID 60071, compound

HRID 1288590Notes

Reaction equation

HRID 1288590 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7]Cl)[CH2:4][CH3:5])[CH3:2].[Na].[OH:10][C:11]1[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=1[O:13][C:14](=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](=[O:17])[CH3:16]>CC(C)=O>[CH2:1]([N:3]([CH2:6][CH2:7][O:10][C:11]1[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=1[O:13][C:14](=[CH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:15](=[O:17])[CH3:16])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 5360545SodiumHCID 54408172HCID 54408172, compound

Product 1

HCID 60071HCID 60071, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21 g of N,N-diethylaminoethyl chloride are added drop by drop to 35 g of the sodium salt of 3-o-hydroxyphenoxy-4-phenyl-3-butene-2-one suspended in 600 cc of anhydrous acetone. The mixture is heated under reflux for 4 hours, the sodium chloride is filtered off, and the filtrate is evaporated to dryness. The residue is dissolved in water and extracted a number of times with diethyl ether. The ether phase, after drying over Na2SO4, is evaporated to dryness and purified by distillation in a bulb apparatus. (B.P. 200°-210°/0.6 mm Hg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe sodium chloride is filtered off
  4. customthe filtrate is evaporated to dryness
  5. dissolutionThe residue is dissolved in water
  6. extractionextracted a number of times with diethyl ether
  7. dry with materialThe ether phase, after drying over Na2SO4
  8. customis evaporated to dryness
  9. distillationpurified by distillation in a bulb apparatus

Sources & evidence

ORD record
ord-0f6881ea52654cabb554b6a8433491ae
Source dataset
uspto-grants-1976_10
Patent number
US03988475

Reaction notes

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