Triethylamine → 6-(4-Isocyanatophenoxy)-hexanoic acid methyl ester

HRID 83790

Reaktionsgleichung

Reaktionsgleichung von HRID 83790
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:26]=[O:28])=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester

Produkt 1

HCID 497644906-(4-Isocyanatophenoxy)-hexanoic acid methyl esterAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To 6-(4-aminophenoxy)-hexanoic acid methyl ester 17 (26 g, 109.7 mmol) and tri-ethylamine (29.2 g, 288.56 mmol) in toluene (390 ml) under nitrogen atmosphere was added triphosgene (15.6 g, 52.56 mmol) in one lot. The reaction was exothermic and internal temperature rose to 60° 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 filtered off, and toluene distilled off under vacuum to get crude 18, which was vacuum distilled to get pure 18 (10 g, 34.7%) with an m.p between 47-50° C.

Aufarbeitung

  1. customrose to 60° C
  2. temperaturemaintained at this temperature for 26 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe solids filtered off
  5. distillationtoluene distilled off under vacuum
  6. customto get crude 18, which
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-b4ad449412b74f6cb1a18470ab4fbd76
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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