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Water → HCID 23350165, Verbindung

HRID 2058277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2058277
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27].[Cl:29][C:30]([SH:33])([Cl:32])[Cl:31].O.ClCCCC.CCCCCC>O1CCCC1>[Cl:29][C:30]([Cl:32])([Cl:31])[S:33][N:12]([C:3]1[CH:4]=[C:5]([C:8]([F:10])([F:9])[F:11])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6390TrichloromethanethiolHCID 12797626FentrifanilHCID 23000051HCID 23000051, Verbindung

Produkt 1

HCID 23350165HCID 23350165, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Sodium hydride (0.6 g, 57% mineral oil), washed free of mineral oil with hexane under a nitrogen atmosphere, is slurried in 25 ml of anhydrous tetrahydrofuran and cooled to 0°. A solution of 2-chloro-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-benzenamine (4.3 g, 0.010 mole) in 25 ml of anhydrous tetrahydrofuran is then added dropwise with stirring at 0°. When the addition is complete, the solution is allowed to warm to ambient temperature and stirred for one hour. Perchloromethyl mercaptan (1.9 g, 0.010 mole) is then added and stirring is continued for two hours. The reaction mixture is then poured into water, extracted with methylene chloride, dried over anhydrous magnesium sulfate and stripped under vacuum to afford an orange resin. Chromatography on silica gel utilizing 1-chlorobutane/hexane (1:1 by vol) as the eluent affords 3.5 g of 1,1,1-trichloro-N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]methanesulfenamide as a yellow oil which crystallizes on standing, m.p. 134°-137°.

Aufarbeitung

  1. washSodium hydride (0.6 g, 57% mineral oil), washed free of mineral oil with hexane under a nitrogen atmosphere
  2. temperaturecooled to 0°
  3. additionWhen the addition
  4. stirringstirred for one hour
  5. stirringstirring
  6. extractionextracted with methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customto afford an orange resin

Quellen und Nachweise

ORD-Eintrag
ord-2911155b851646088d1ca56378d7c876
Quelldatensatz
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04215145

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