Ethanolamine → N-(2-hydroxyethyl)-N-(2-hydroxypropyl)-4,4,4-trichloro-2-hydroxy-1-butylamine
Reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]1[O:8][CH:6]1[CH3:7].[Cl:9][C:10]([Cl:16])([Cl:15])[CH2:11][CH:12]1[O:14][CH2:13]1.CO>C(O)(C)C>[OH:2][CH2:1][CH2:3][N:4]([CH2:13][CH:12]([OH:14])[CH2:11][C:10]([Cl:16])([Cl:15])[Cl:9])[CH2:5][CH:6]([OH:8])[CH3:7]Participants
Procedure
To a solution of 30.6g (0.5 mole) monoethanolamine in 150 ml isopropanol heated to reflux was slowly added 33.8g (0.58 mole) propylene oxide over a period of about one hour. After refluxing the mixture overnight the solvent and unreacted starting material were distilled off, affording a residue weighing 49.1g. To this residue was added 5.7g of the unreacted monoethanolamine distillate. To this mixture was added 90g (0.51 mole) 4,4,4-trichloro-1,2-epoxybutane over a period of 45 minutes. An equivolume amount of methanol was then added and the reaction mixture refluxed overnight. Evaporation of the solvent yielded 140.8g (95.5%) of N-(2-hydroxyethyl)-N-(2-hydroxypropyl)-4,4,4-trichloro-2-hydroxy-1-butylamine, a brown viscous liquid very soluble in methanol but only slightly soluble in water(pH 7-8); hydroxyl number = 564. Analysis: (Calculated) %N 4.79; %Cl, 36.35. (Found) %N, 4.56; %Cl, 36.92.
Workup
- temperatureto reflux
- customof about one hour
- temperatureAfter refluxing the mixture overnight the solvent
- distillationwere distilled off
- customaffording a residue
- temperaturethe reaction mixture refluxed overnight
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-50585243b7b24192a620a7709a61ec02
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04110379
Reaction notes
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