O-Xylene → 4,8-Bis(trifluoromethyl)-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one

HRID 974813

반응식

HRID 974813 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12][C:13]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#N.[OH-:25].[Na+].C1(C)C(C)=CC=CC=1>C(O)(=O)C.S(=O)(=O)(O)O.O>[F:23][C:21]([F:24])([F:22])[C:20]1[C:13]2[S:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[NH:1][C:15](=[O:25])[C:14]=2[CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 3

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 199694362-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile

생성물 1

HCID 199694574,8-Bis(trifluoromethyl)-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

2-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile (5.43 g, 15 mmol) was dissolved in a mixture of glacial acetic acid (60 ml), concentrated sulphuric acid (55 ml) and water (60 ml) and then heated under reflux for 8 hours. The cooled mixture was added to ice water (500 ml) and brought to pH 4 by addition of 10N aqueous sodium hydroxide. Extraction with dichloromethane followed by filtration, drying (sodium sulphate) and evaporation of the organic layer afforded a residue which was put into xylene (500 ml) and refluxed for 72 hours with azeotropic removal of water. The resulting solution was evaporated and the residue was recrystallised twice from ethanol to give the product as colourless needles (4.30 g, m/s, M+ =363).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. extractionExtraction with dichloromethane
  4. filtrationfollowed by filtration
  5. customdrying
  6. custom(sodium sulphate) and evaporation of the organic layer
  7. customafforded a residue which
  8. customThe resulting solution was evaporated
  9. customthe residue was recrystallised twice from ethanol

출처 및 근거

ORD 기록
ord-17e84a3c41ea44e3a4633a93a698b915
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05607929

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