1,4-Dioxane → 2-(4-Isocyanatophenoxy)-propionic acid 2-[2-(4-isocyanatophenoxy)-propionyloxy]-ethyl ester
Reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH:7]([CH3:26])[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:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.[O:41]1CCOC[CH2:42]1>>[N:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH:15]([CH3:16])[C:14]([O:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[CH:7]([O:6][C:5]2[CH:27]=[CH:28][C:2]([N:1]=[C:42]=[O:41])=[CH:3][CH:4]=2)[CH3:26])=[O:25])=[CH:23][CH:22]=1)=[C:30]=[O:32]Participants
4
Conditions
- Temperature
- 77.5 °C
Procedure
2-(4-Aminophenoxy)propionic acid-2-[2-(4-aminophenoxy)propionyloxy]ethyl ester 50 (5.3 g, 13.6 mmol) was dissolved in dry dioxane (80 ml) under nitrogen atm. and cooled below 20° C. A solution of triphosgene (7 g, 23.6 mmol) in dry dioxane (20 ml) was added dropwise. The mixture was heated slowly to 75-80° C. and maintained for 2½ hours. The condenser was then arranged for distillation and solvent removed by distillation at atmospheric pressure until the volume of reaction mixture was reduced to approximately one third. Fresh dry dioxane (50 ml) was added and the solvents were distilled off under vacuum. The residue was re-evaporated two times from dry dioxane to give pure 51 (4 g, 66.5%) as a light brown liquid.
Workup
- temperatureand cooled below 20° C
- temperaturemaintained for 2½ hours
- distillationThe condenser was then arranged for distillation and solvent
- customremoved by distillation at atmospheric pressure until the volume of reaction mixture
- additionFresh dry dioxane (50 ml) was added
- distillationthe solvents were distilled off under vacuum
- customThe residue was re-evaporated two times from dry dioxane
Sources & evidence
- ORD record
- ord-951cbeec96f34f01b4bb389b3eff5feb
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691364B2
Reaction notes
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