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

HRID 638725

Reaktionsgleichung

Reaktionsgleichung von HRID 638725
[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 a mixture of 6-(4-amino-phenoxy) hexanoic acid methyl ester 21 (26 grams, 109.7 mmol) and triethylamine (29.2 g, 288.56 mmol) in toluene (390 ml) under nitrogen atm. was added triphosgene (15.6 grams, 52.56 mmol) in one lot. The reaction was exothermic and the 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 were filtered, and the toluene was distilled off under vacuum to get crude 36, which was vacuum distilled to get pure 36 (10 g, 34.7%). M.p: 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 were filtered
  5. distillationthe toluene was distilled off under vacuum
  6. customto get crude 36, which
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-cf37ab8dbac84da9a6c6b8284979948b
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691364B2

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