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

HRID 1098705Notes

Reaction equation

HRID 1098705 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 temperature 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 temperature 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-bad4376df2b44d199ac320dc76160d6f
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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