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2,6-Xylyl isothiocyanate → N-(2,6-Dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

HRID 1032099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1032099
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.C(N1CC(OC2C=CC=C(C(F)(F)F)C=2)C1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:46]=1[N:52]=[C:53]=[S:54]>C(Cl)Cl>[CH3:51][C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([CH3:44])[C:46]=1[NH:52][C:53]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[CH2:8]1)=[S:54]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 879762,6-Xylyl isothiocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidineHCID 117286941-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine

Produkt 1

HCID 15053383N-(2,6-Dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

Crude 3-[3-(trifluoromethyl)phenoxy]azetidine from catalytic debenzylation of 30.0 g (0.078 mole) of 1-benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine was dissolved in 100 ml of methylene chloride and treated dropwise under a nitrogen atmosphere with a solution of 12.7 g (0.078 mole) of 2,6-dimethylphenylisothiocyanate in 25 ml of methylene chloride. The product began to precipitate during the addition and an additional 50 ml of methylene chloride was added to facilitate stirring. After stirring overnight at ambient temperature, the product was collected by filtration (13.5 g, m.p. 196°-199° C.). A 6.0 g sample was recrystallized from isopropanol to give 5.3 g of product, m.p. 197°-199° C.

Aufarbeitung

  1. customto precipitate during the addition
  2. additionan additional 50 ml of methylene chloride was added
  3. stirringAfter stirring overnight at ambient temperature
  4. filtrationthe product was collected by filtration (13.5 g, m.p. 196°-199° C.)
  5. customA 6.0 g sample was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-7bbf08df0a04472389d576c1149ade50
Quelldatensatz
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04956359

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