Toluene → N-(2-(2,4,6-Trichlorophenoxy)ethyl)-1-propanamine

HRID 1906748

Reaction equation

[CH2:1]([NH:4][C:5](=O)[CH2:6][O:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH2:2][CH3:3].C1(C)C=CC=CC=1.CSC.B>CO>[Cl:14][C:13]1[CH:12]=[C:11]([Cl:15])[CH:10]=[C:9]([Cl:16])[C:8]=1[O:7][CH2:6][CH2:5][NH:4][CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(n-propyl)-2,4,6-trichlorophenoxyacetamide, 44.0 gm, was added to 250 ml of toluene. 28 ml of borane methyl sulfide [BH3.(CH3)2S] (2 equivalents) was then slowly added to the system. The system was heated at approximately 60° C. for 15 hours at which time reaction completion was checked by IR spectroscopy. 200 ml of methanol was then slowly added to the system. After addition of the methanol, the system was acidified by bubbling in HCl gas. Afterwards, the system was refluxed for 1 hour. The solvent was then removed by stripping. The resulting oil was dissolved in methanol which was then stripped. The oil was next dissolved in methylene chloride. The organic solution was washed with a sodium hydroxide solution and then with water. The methylene chloride was removed by stripping to give 36.3 gm of the N-(n-propyl) ethanolamine 2,4,6-trichlorophenylether, as a yellow oil.

Workup

customby bubbling in HCl gas
temperatureAfterwards, the system was refluxed for 1 hour
customThe solvent was then removed by stripping
dissolutionThe resulting oil was dissolved in methanol which
dissolutionThe oil was next dissolved in methylene chloride
washThe organic solution was washed with a sodium hydroxide solution
customThe methylene chloride was removed

Sources & evidence

ORD record: ord-4f44e41b87c54988a286558387ddeb5f
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04654346

Linked notes

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