Hydrochloric Acid → HCID 66957906, Verbindung

HRID 215718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 215718
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:17]([S:18][CH3:19])=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:24]1(=O)[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1.C(N(CC)CC)C.Cl>CN(C)C=O.ClCCl>[CH3:7][O:8][C:9]1[C:17]([S:18][CH3:19])=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:14][C:10]=1[C:11]([O:13][C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)=[O:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 669579072-Methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 66957906HCID 66957906, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

133 mg (1.05 mmol) of oxalyl dichloride and three drops of N,N-dimethylformamide were added in succession to 200 mg (purity 78% by weight, 0.59 mmol) of 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid in 20 ml of dichloromethane. After the elimination of gas had ceased, the mixture was heated under reflux for another 10 min. The content was then cooled to RT and freed from the solvent. 93 mg (0.83 mmol) of 1,3-cyclohexanedione were added to the residue in 20 ml of dry dichloromethane, and 152 mg (1.50 mmol) of triethylamine were then added dropwise. The mixture was stirred at RT for 16 h. For work-up, 3 ml of 1M hydrochloric acid were added to the contents. After phase separation, the organic phase was freed from the solvent. The residue was purified chromatographically, which isolated 100 mg of 3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for another 10 min
  3. customAfter phase separation
  4. customThe residue was purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-4070c308f2f64353b9bdaddc1bc4a3d9
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193121B2

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