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

HRID 974813
Notes
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Reaction equation

HRID 974813 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent
HCID 962
Water
Solvent
2×
HCID 1118Sulfuric AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-17e84a3c41ea44e3a4633a93a698b915
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05607929

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes