O-ethylhydroxylamine hydrochloride → O-ethyl-N-(2,4,6-trichlorophenoxy)ethylhydroxylamine hydrochloride

HRID 2118544Notes

Reaction equation

HRID 2118544 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[O:4][CH2:5][CH2:6]Br.Cl.[CH2:15]([O:17][NH2:18])[CH3:16]>C(N(C(C)C)C(C)C)C>[ClH:1].[CH2:15]([O:17][NH:18][CH2:6][CH2:5][O:4][C:3]1[C:2]([Cl:1])=[CH:11][C:10]([Cl:12])=[CH:9][C:8]=1[Cl:13])[CH3:16]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 135651032-(2-Bromoethoxy)-1,3,5-trichlorobenzene

Product 1

HCID 85519368O-ethyl-N-(2,4,6-trichlorophenoxy)ethylhydroxylamine hydrochlorideYield 105.9%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
50 °C

Procedure

30.4 g (0.1 mole) of 2,4,6-trichlorophenoxyethyl bromide were added to a suspension of 48.5 g (0.5 mole) of O-ethylhydroxylamine hydrochloride in 250 ml of ethyldiisopropylamine, and the mixture was stirred for 4 days at 50° C. and then cooled to 15° C. and filtered under suction. The filtrate was evaporated down under reduced pressure, in the final stage at 60° C. and under 0.1 mbar, the residue was dissolved in 300 ml of ether, and the solution was gassed with hydrogen chloride at +3° C. 17 g of O-ethyl-N-(2,4,6-trichlorophenoxy)ethylhydroxylamine hydrochloride of melting point 173°-175° C. were obtained.

Workup

  1. temperaturecooled to 15° C.
  2. filtrationfiltered under suction
  3. customThe filtrate was evaporated down under reduced pressure
  4. dissolutionin the final stage at 60° C. and under 0.1 mbar, the residue was dissolved in 300 ml of ether
  5. customwas gassed with hydrogen chloride at +3° C

Sources & evidence

ORD record
ord-991487f18eba4c268c3883c4c47b1005
Source dataset
uspto-grants-1987_07
Patent number
US04678798

Reaction notes

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