Trifluoroacetic acid → HCID 21438364, compound

HRID 329256Notes

Reaction equation

HRID 329256 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2(O)[C:21]3[CH:20]=[C:19]([S:22][C:23]([F:26])([F:25])[F:24])[CH:18]=[CH:17][C:16]=3[S:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.FC(F)(F)C(O)=O>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:21]3[CH:20]=[C:19]([S:22][C:23]([F:25])([F:24])[F:26])[CH:18]=[CH:17][C:16]=3[S:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 21438369HCID 21438369, compound

Product 1

HCID 21438364HCID 21438364, compound

Procedure

A solution of 3.29 g. of 1-methyl-4-(2-trifluoromethylthio-9-hydroxy-thioxanthen-9-yl)piperidine in 15 ml. of trifluoroacetic anhydride and 30 ml. of trifluoroacetic acid is stirred and refluxed for 2.5 hours. The solution is evaporated to dryness. The residue is dissolved in benzene and is washed with 10% sodium hydroxide to make the free base form. The benzene is washed with water, dried over magnesium sulfate, filtered and the benzene is removed on a rotary evaporator. The residue is recrystallized from acetonitrile to give 1-methyl-4-[2-(trifluoromethylthio)thioxanthen-9-ylidene]piperidine, m.p. 104°-106° C.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. customThe solution is evaporated to dryness
  3. dissolutionThe residue is dissolved in benzene
  4. washis washed with 10% sodium hydroxide
  5. washThe benzene is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe benzene is removed on a rotary evaporator
  9. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d06ff129601b4b93a615a94f9c5a697b
Source dataset
uspto-grants-1977_04
Patent number
US04020169

Reaction notes

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