Phosgene → 2-Chloro-6-(4-isocyanatophenoxy)pyridine

HRID 1415089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1415089
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]=[C:1]=[O:2])=[CH:15][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 6371Phosgene3×HCID 13980869Benzenamine, 4-[(6-chloro-2-pyridinyl)oxy]-

Produkt 1

HCID 213914912-Chloro-6-(4-isocyanatophenoxy)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A stream of phosgene was passed into 120 ml. of dry toluene maintained at a temperature of about 0° to about 5° C. until a weight of 13.4 grams (0.135 mole) had been absorbed. 4-((6-Chloro-2-pyridinyl)oxy)benzenamine (10.0 grams; 0.045 mole) in 100 ml. of dry toluene was then added to the stirred phosgene solution over a period of about 15 minutes while maintaining the reaction temperature within a range of about 2° to about 5° C. Following the completion of the addition, the reaction mixture was stirred for about 20 minutes and the reaction temperature then gradually raised as excess phosgene was purged with a stream of nitrogen. When a reaction temperature of about 85° C. was attained, the reaction mixture became clear. The toluene solvent was then substantially removed under reduced pressure and hexane added to the residue to give the desired 4-((6-chloro-2-pyridinyl)oxy)phenyl isocyanate product as a white crystalline product having a melting point of 96°-97° C.

Aufarbeitung

  1. customhad been absorbed
  2. temperaturewhile maintaining the reaction temperature within a range of about 2° to about 5° C
  3. additionthe completion of the addition
  4. customwas purged with a stream of nitrogen
  5. customa reaction temperature of about 85° C.
  6. customThe toluene solvent was then substantially removed under reduced pressure and hexane
  7. additionadded to the residue

Quellen und Nachweise

ORD-Eintrag
ord-3f8ce0dae1934b2b8f8bb25b3f1250f6
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04003734

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