1,3-Dichloro-2-isothiocyanatobenzene → N-(2,6-Dichlorophenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

HRID 974553

Reaktionsgleichung

Reaktionsgleichung von HRID 974553
[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.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[N:24]=[C:25]=[S:26].[N-]=C=S>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[NH:24][C:25]([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:26]

Komponenten

5

Edukt 3

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidineHCID 178418790HCID 178418790, Verbindung

Produkt 1

HCID 15053384N-(2,6-Dichlorophenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamideAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 0.04 mole of 3-[3-(trifluoromethyl) phenoxy]azetidine in 100 ml of absolute ethanol was stirred in a tap water bath while 8.16 g (0.04 mole) of 2,6-dichlorophenyl isothiocyanate was added all at once. The reaction was slightly exothermic and as the isothiocyanate began to dissolve, product began to precipitate. After stirring for 45 minutes the reaction mixture was heated on a steam bath to assure that all the isothiocyanate dissolved, and upon cooling, filtration yielded 15.2 g of white crystalline product. A portion of this material (7.9 g) was recrystallized from absolute ethanol to give 4.3 g of pure crystalline powder, m.p. 196°-197° C.

Aufarbeitung

  1. additionwas added all at once
  2. dissolutionto dissolve
  3. customto precipitate
  4. temperaturewas heated on a steam bath
  5. dissolutiondissolved
  6. temperatureupon cooling
  7. filtrationfiltration

Quellen und Nachweise

ORD-Eintrag
ord-2889d763bd8c4d559d166dcd12d8d557
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068231

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