Triethylamine → HCID 21482160, compound

HRID 1415404Notes

Reaction equation

HRID 1415404 reaction equation
[Cl-].[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[O:5][CH:6]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][NH+:8]([CH2:11][CH3:12])[CH2:9][CH3:10].C(N(CC)CC)C>O1CCCC1>[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[O:5][CH:6]([C:13](=[O:18])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21482164HCID 21482164, compound

Product 1

HCID 21482160HCID 21482160, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38.1 g (0.1 mole) of [2-(2,4-dichlorophenoxy)-4,4-dimethyl-pentan-3-onyl]-diethylammonium chloride were dissolved in 200 ml of anhydrous tetrahydrofuran and 20.2 g (0.2 mole) of triethylamine were added dropwise at room temperature. After stirring for quarter of an hour at room temperature, the triethylammonium chloride which had precipitated was filtered off and the solvent was distilled off in vacuo. 30.9 g (90% of theory) of [2-(2,4-dichlorophenoxy)-4,4-dimethyl-pentan-3-onyl]-diethylamine were obtained as a yellow oil, which was immediately dissolved in 300 ml of anhydrous acetonitrile (0.09 molar batch). 21.3 g (0.15 mole) of methyl iodide were added dropwise thereto at room temperature, while stirring. The reaction mixture was stirred for 1 hour at room temperature and for 30 minutes under reflux and thereafter the solvent was distilled off under reduced pressure. The oil residue was taken up in 200 ml of a mixture of ethyl acetate and methyl ethyl ketone (1:1) and the whole was heated to the boil. This produced a crystalline residue, which was filtered off and rinsed with ether. 22.8 g (51.6% of theory) of [2-(2,4-dichlorophenoxy)-4,4-dimethyl-pentan-3-onyl]-diethylmethylammonium iodide of melting point 114°-118° C were obtained. ##STR155##

Workup

  1. customthe triethylammonium chloride which had precipitated
  2. filtrationwas filtered off
  3. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-ac547f5f7a07422a9751e3596a3d23e9
Source dataset
uspto-grants-1977_01
Patent number
US04005083

Reaction notes

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