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

HRID 400097

反応式

HRID 400097 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e77ea16219d743749f81a921a7f27660
出典データセット
uspto-grants-1998_10
特許番号
US05827856

関連ノート

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