Triethylamine → 2-(4-Isocyanato-phenoxy)-propionic acid methyl ester

HRID 83783Notes

Reaction equation

HRID 83783 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:5].C(N(CC)CC)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:23]=[O:25])=[CH:9][CH:8]=1)[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22060471Methyl 2-(4-aminophenoxy)propanoate

Product 1

HCID 497643632-(4-Isocyanato-phenoxy)-propionic acid methyl esterYield 143.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 2-(4-aminophenoxy)-propionic acid methyl ester 10 (15 g, 76.9 mmol) and triethylamine (15.6 g, 154.16 mmol) in toluene (210 ml) under nitrogen atmosphere was added triphosgene (8.4 g, 28.3 mmol) in one lot. Later the reaction mixture was heated to 75° C. over a period of one hour and maintained at this tempera-ture for 26 hours. The reaction mixture was cooled to room temperature, the solids filtered off, and the toluene was distilled off under vacuum to get crude 11, which was vacuum distilled to get pure 11 (9 grams, 52.9%) as a light yellow syrup.

Workup

  1. temperaturemaintained at this tempera-ture for 26 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solids filtered off
  4. distillationthe toluene was distilled off under vacuum
  5. customto get crude 11, which
  6. distillationdistilled

Sources & evidence

ORD record
ord-5bb5f911646948b0a3751af8085b9d82
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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