Water → 3-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

HRID 974545

Reaktionsgleichung

Reaktionsgleichung von HRID 974545
[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][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:19]2)C=CC=CC=1.O>C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH:20]2[CH2:19][N:18]([C:1]([Cl:4])=[O:2])[CH2:21]2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 150533691-Benzhydryl-3-(4-fluorophenoxy)azetidine

Produkt 1

HCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 52.09 g (0.527 mole) of phosgene in 500 ml of methylene chloride was stirred with 73 g (0.53 mole) of potassium carbonate under nitrogen atmosphere for 30 min, then treated with 146.3 g (0.439 mole) of 1-diphenylmethyl-3-(4-fluorophenoxy)azetidine in 300 ml of methylene chloride added dropwise. After stirring for 18 hr, the reaction mixture was treated with 200 ml of water added slowly. The aqueous phase was separated and the organic solution dried by filtration through Whatman phase separating filter paper then concentrated in vacuo to a pale amber oil. Trituration of the oil with 30/60 petroleum ether yielded a crude tacky solid, 89.3 g (88.6%). A portion of this solid was recrystallized from 30/60 petroleum ether yielding a fine white crystalline product, m.p. 44°-52° C. A second recrystallization from isopropyl ether yielded fine white crystals, m.p. 57°-58.5° C.

Aufarbeitung

  1. additionadded dropwise
  2. additionadded slowly
  3. customThe aqueous phase was separated
  4. customthe organic solution dried by filtration through Whatman phase
  5. customseparating
  6. filtrationfilter paper
  7. concentrationthen concentrated in vacuo to a pale amber oil
  8. customTrituration of the oil with 30/60 petroleum ether yielded a crude tacky solid, 89.3 g (88.6%)
  9. customA portion of this solid was recrystallized from 30/60 petroleum ether yielding a fine white crystalline product, m.p. 44°-52° C
  10. customA second recrystallization from isopropyl ether yielded fine white crystals, m.p. 57°-58.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-c79644b79d5a48aea1c5f779fe3709ef
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068231

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