Sulfuric Acid → 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-thiol
Reaction equation
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]=1Participants
Procedure
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.
Workup
- temperatureheated
- temperatureat reflux temperature for 2.5 h
- temperaturethe mixture was subsequently heated
- temperatureto reflux temperature under a nitrogen atmosphere for 2 h
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with diethyl ether (50 ml)
- washThe organic phase was washed with water (50 ml) and brine (30 ml)
- customEvaporation in vacuo
Sources & evidence
- ORD record
- ord-e77ea16219d743749f81a921a7f27660
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05827856
Reaction notes
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