1,4-Dioxane → 2-(4-Isocyanatophenoxy)propionic acid-2-[2-(4-isocyanatophenoxy)acetoxy]ethyl ester
Reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH2:12][O:13][C:14](=[O:25])[CH:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH3:16])=[O:9])=[CH:4][CH:3]=1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.[O:40]1CCOC[CH2:41]1>>[N:1]([C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH2:12][O:13][C:14](=[O:25])[CH:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]=[C:41]=[O:40])=[CH:22][CH:23]=2)[CH3:16])=[O:9])=[CH:4][CH:3]=1)=[C:29]=[O:31]Participants
4
Conditions
- Temperature
- 77.5 °C
Procedure
2-(4-Aminophenoxy)-propionic acid 2-[2-(4-aminophenoxy)-acetoxy]-ethyl ester 39 (5.2 g, 13.9 mmol) was dissolved in dry dioxane (80 ml) under nitrogen atmosphere and cooled to below 20° C. A solution of triphosgene (7 g, 23.6 mmol) in dry dioxane (20 ml) was added drop wise. The mixture was heated slowly to 75-80° C. and main-tained for 3 hrs. A condenser was then arranged for distillation and solvent removed by distillation at atmospheric pressure until the volume of the reaction mixture was reduced to approximately one third. Fresh dry dioxane (50 ml) was added and the solvent was distilled off under vacuum. The residue was re-evaporated two times from dry dioxane to give 40 (2.2 g, 37.2%) as a light yellow syrup.
Workup
- temperaturecooled to below 20° C
- distillationA condenser was then arranged for distillation and solvent
- customremoved by distillation at atmospheric pressure until the volume of the reaction mixture
- additionFresh dry dioxane (50 ml) was added
- distillationthe solvent was distilled off under vacuum
- customThe residue was re-evaporated two times from dry dioxane
Sources & evidence
- ORD record
- ord-ce8a8a1569de4b0593bf85a4f59b4219
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846845B2
Reaction notes
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