Phosgene → 1-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

HRID 974549

Reaktionsgleichung

Reaktionsgleichung von HRID 974549
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][CH:20]1[CH2:21][N:18]([C:1]([Cl:4])=[O:2])[CH2:19]1

Komponenten

5

Edukt 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 117286941-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine

Produkt 1

HCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 35.6 g (0.36 mole) of phosgene in 200 ml of methylene chloride at 5° C. was stirred with 50 g (0.36 mole) of potassium carbonate for 1 hr. To the mixture was added dropwise 115 g (0.3 mole) of 1-diphenylmethyl-3-[-3-(trifluoromethyl)phenoxy]azetidine in 400 ml of methylene chloride. After stirring for 18 hr, the reaction mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and concentrated on a rotary evaporator to a viscous oil residue, 133.2 g. Trituration of the residue with hexane gave a solid which was recrystallized from cold hexane to yield 52 g (62%) of white crystals, m.p. 72.5°-74° C.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator to a viscous oil residue, 133.2 g
  5. customTrituration of the residue with hexane gave a solid which
  6. customwas recrystallized from cold hexane

Quellen und Nachweise

ORD-Eintrag
ord-af588826d4cf4c0aaa532385c2c04d5a
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068231

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