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

HRID 400097

반응식

HRID 400097 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e77ea16219d743749f81a921a7f27660
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827856

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