1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 21318116, compound

HRID 263081Notes

Reaction equation

HRID 263081 reaction equation
Cl.[CH2:2]([N:4]([CH2:7][CH2:8][Cl:9])[CH2:5][CH3:6])[CH3:3].[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1.[OH-].[Na+]>O.C(O)C>[ClH:9].[CH2:5]([N:4]([CH2:7][CH2:8][O:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:14]2[CH:23]=[CH:24][C:11]([Cl:10])=[CH:12][CH:13]=2)=[CH:21][CH:20]=1)[CH2:2][CH3:3])[CH3:6]

Participants

6

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium HydroxideHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 21318116HCID 21318116, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 13.2 g (0.075 mol) of 2-(N,N-diethylamino)-1-chloroethane hydrochloride in 30 ml of water is run over the course of 30 minutes into a solution, kept at about 60° C., of 15 g (0.068 mol) of p-(p-chlorophenoxy)-phenol and 6.3 g (0.157 mol) of sodium hydroxide pellets in 20 ml of water and 20 ml of ethanol. The mixture is heated to the reflux temperature for 1 hour and the ethanol is evaporated under reduced pressure. The aqueous phase is extracted with diethyl ether and the organic phase obtained is washed with water until neutral, dried over dry sodium sulphate and evaporated to dryness under reduced pressure. The oily residue is treated in a solution of hydrogen chloride in diethyl ether, to give 20 g of a white powder. Recrystallisation from ethyl acetate gives 18 g of CRL 40 330

Workup

  1. customis run over the course of 30 minutes into a solution
  2. temperatureThe mixture is heated to the reflux temperature for 1 hour
  3. customthe ethanol is evaporated under reduced pressure
  4. extractionThe aqueous phase is extracted with diethyl ether
  5. customthe organic phase obtained
  6. washis washed with water until neutral,
  7. dry with materialdried over dry sodium sulphate
  8. customevaporated to dryness under reduced pressure
  9. additionThe oily residue is treated in a solution of hydrogen chloride in diethyl ether

Sources & evidence

ORD record
ord-2fe8295884c74e5796c62d56892dcd3d
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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