Acetic Acid → 4-(2,6-Dichloro-4-trifluoromethylphenyl)-2-isopropylthioaniline

HRID 25295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25295
O.C(O)(=O)C.[CH:6]([S:9][C:10]1[CH:15]=[C:14]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[CH:13]=[CH:12][C:11]=1[N+:28]([O-])=O)([CH3:8])[CH3:7].C(SC1C=C(C2C(C(F)(F)F)=NNC=2)C=CC=1C(OC)=O)CC>C1(C)C=CC=CC=1.[Fe]>[Cl:27][C:17]1[CH:18]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:20]=[C:21]([Cl:22])[C:16]=1[C:14]1[CH:13]=[CH:12][C:11]([NH2:28])=[C:10]([S:9][CH:6]([CH3:8])[CH3:7])[CH:15]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 22170887[5-(2,6-Dichloro-4-trifluoromethylphenyl)-2-nitrophenyl]isopropyl sulfideHCID 178460720HCID 178460720, Verbindung

Produkt 1

HCID 221709304-(2,6-Dichloro-4-trifluoromethylphenyl)-2-isopropylthioanilineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

3.5 g (63.6 mmol) of iron powder, 10 m of water and 1 m of acetic acid were stirred in 20 ml toluene at 60° C. for 30 minutes, and 3.0 g (7.3 mmol) of [5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrophenyl] isopropyl sulfide (the compound prepared in Example 8 (2)) in 10 ml toluene was added dropwise. The reaction was carried out with reflux and heating for another 3 hours, and then the reaction mixture was cooled to room temperature. The insolubles were filtered off, and the filtrate was separated with water and toluene. The toluene layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.0 g of 4-(2,6-dichloro-4-trifluoromethylphenyl)-2-isopropylthioaniline (yield 36.0%) as a pale yellow dough (nD20 1.5782).

Aufarbeitung

  1. temperaturewith reflux
  2. temperatureheating for another 3 hours
  3. filtrationThe insolubles were filtered off
  4. customthe filtrate was separated with water and toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customPurification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d2aa7a5464aa4339ae0dedd26dc4e278
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858639B2

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