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

HRID 1957839Notes

Reaction equation

HRID 1957839 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 18 (15 grams, 76.9 mmol) and triethylamine (15.6 g, 154.16 mmol) in toluene (210 ml) under nitrogen atm. 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 temp. for 26 hours. The reaction mixture was cooled to room temperature, the solids were filtered off, and the toluene was distilled off under vacuum to get crude 32, which was vacuum distilled to get pure 32 (9 g, 52.9%) as a light yellow syrup.

Workup

  1. temperaturemaintained at this temp
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solids were filtered off
  4. distillationthe toluene was distilled off under vacuum
  5. customto get crude 32, which
  6. distillationdistilled

Sources & evidence

ORD record
ord-1d74137f1d994c8b8363deb9efcd162a
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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