Triethylamine → (4-Isocyanato-phenoxy)-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]=[C:22]=[O:24])=[CH:8][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a mixture of (4-Amino-phenoxy)-acetic acid methyl ester 15 (15 g, 82.87 mmol) and triethylamine (16.77 g, 165.73 mmol) in toluene (225 ml) under nitrogen atm. at 0° C. was added triphosgene (9 g, 30.33 mmol) in one lot. The reaction was exothermic and the temperature raised to 25° C. Later the reaction mixture was heated to 75° C. over a period of one hour and maintained at this temperature for 26 hours. The reaction mixture was then cooled to room temperature, the solids were filtered off, and the toluene was distilled off under vacuum to get crude 28, which was vacuum distilled to get pure 28 (10 g, 58.3%) as a white powder. M.p: 50-53° C.
Workup
- temperatureLater the reaction mixture was heated to 75° C. over a period of one hour
- temperaturemaintained at this temperature for 26 hours
- temperatureThe reaction mixture was then cooled to room temperature
- filtrationthe solids were filtered off
- distillationthe toluene was distilled off under vacuum
- customto get crude 28, which
- distillationdistilled
Sources & evidence
- ORD record
- ord-0f2a729f371b4e159960c40dbc7d47a9
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08409559B2
Reaction notes
Loading…