Trifluoroacetic acid → 5-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

HRID 1576623Notes

Reaction equation

HRID 1576623 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][C:6]1(O)[C:12]2[CH:13]=[C:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]1=2.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[C:14]([S:17]([CH3:20])(=[O:18])=[O:19])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]1=2

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 214120875-(3-dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 494065-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

Conditions

Temperature
70 °C

Procedure

5-(3-Dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene (13.62 g., 0.037 mole) is dissolved in 136 ml. of trifluoroacetic acid. Trifluoroacetic anhydride, 68 ml., is added and the solution heated under reflux for 1 hour in a water-bath at 70°C. The dark green solution is cooled and poured into 250 ml. of ice-water. The mixture is rendered alkaline with 10 N. sodium hydroxide solution while stirring and cooling and extracted with benzene. The benzene extract is washed with water, dried over sodium sulfate and the benzene distilled under reduced pressure. The mixed geometric isomers of 5-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene is obtained as a brown oily residue in a yield of 13.19 g. (theory, 13.08 g.).

Workup

  1. addition, is added
  2. temperaturethe solution heated
  3. temperatureThe dark green solution is cooled
  4. additionpoured into 250 ml
  5. temperaturecooling
  6. extractionextracted with benzene
  7. extractionThe benzene extract
  8. washis washed with water
  9. dry with materialdried over sodium sulfate
  10. distillationthe benzene distilled under reduced pressure

Sources & evidence

ORD record
ord-e8d442f5fe3842edac2362f60fc58739
Source dataset
uspto-grants-1976_09
Patent number
US03981917

Reaction notes

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