Triethylamine → (4-Isocyanato-phenoxy)-acetic acid methyl ester

HRID 83775

Reaction equation

HRID 83775 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]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 6422115Methyl(4-aminophenoxy)acetate

Product 1

HCID 18918618(4-Isocyanato-phenoxy)-acetic acid methyl esterYield 159.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of (4-aminophenoxy)-acetic acid methyl ester 3 (15 g, 82.87 mmol) and triethylamine (16.77 g, 165.73 mmol) in toluene (225 ml) under nitrogen atmosphere at 0° C. was added triphosgene (9 g, 30.33 mmol) in one lot. The reaction was exo-thermic and the temperature rose 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 cooled to room temperature, the solids were filtered off, and toluene was distilled off under vacuum to get crude 4, which was vacuum distilled to get pure 4 (10 grams, 58.3%) as a white powder with an m.p between 50-53° C.

Workup

  1. customrose to 25° C
  2. temperaturemaintained at this temperature for 26 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe solids were filtered off
  5. distillationtoluene was distilled off under vacuum
  6. customto get crude 4, which
  7. distillationdistilled

Sources & evidence

ORD record
ord-3b5f043239244cea8c03e1d5a5f191d8
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Linked notes

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