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

HRID 1082075
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HRID 1082075 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 물질실험 절차후처리출처 및 근거반응 노트

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 962
Water
용매
2회
HCID 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 reflex 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 under reflex for 8 hours
  2. extractionExtraction with dichloromethane
  3. filtrationfollowed by filtration
  4. customdrying
  5. custom(sodium sulphate) and evaporation of the organic layer
  6. customafforded a residue which
  7. customThe resulting solution was evaporated
  8. customthe residue was recrystallised twice from ethanol

출처 및 근거

ORD 기록
ord-63e5b92100d649e4abe24fe83234f05b
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05589474

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