Sulfuric Acid → 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-thiol

HRID 400097

Reaktionsgleichung

Reaktionsgleichung von HRID 400097
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.NC(N)=[S:19].[OH-].[Na+].S(=O)(=O)(O)O>C(O)C>[CH:13]1[C:4]2[CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]([SH:19])[C:3]=2[CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-HCID 14798Sodium HydroxideHCID 2723790Thiourea

Produkt 1

HCID 1894394510,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-thiolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

5-Chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (6.86 g, 0.030 mol) and thiourea (2.28 g, 0.030 mol) were dissolved in ethanol (50 ml) and heated at reflux temperature for 2.5 h. After cooling to room temperature, 2 N sodium hydroxide (20 ml) was added and the mixture was subsequently heated to reflux temperature under a nitrogen atmosphere for 2 h. The reaction mixture was cooled to room temperature, made acidic by addition of a slight excess of sulfuric acid and extracted with diethyl ether (50 ml). The organic phase was washed with water (50 ml) and brine (30 ml). Evaporation in vacuo afforded 6.78 g (100%) of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-thiol as an oil . The crude product was directly used in the next step without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 h
  3. temperaturethe mixture was subsequently heated
  4. temperatureto reflux temperature under a nitrogen atmosphere for 2 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionextracted with diethyl ether (50 ml)
  7. washThe organic phase was washed with water (50 ml) and brine (30 ml)
  8. customEvaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e77ea16219d743749f81a921a7f27660
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827856

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