4-(2,2,2-Trifluoroethoxy)aniline → HCID 86685406, compound

HRID 570750Notes

Reaction equation

HRID 570750 reaction equation
[N:1]([C:4]1[C:5]([C:9]([O:11]CC)=O)=[CH:6][S:7][CH:8]=1)=[C:2]=[S:3].[F:14][C:15]([F:26])([F:25])[CH2:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>C(#N)C.C(O)C>[S:3]=[C:2]1[NH:1][C:4]2=[CH:8][S:7][CH:6]=[C:5]2[C:9](=[O:11])[N:22]1[C:21]1[CH:23]=[CH:24][C:18]([O:17][CH2:16][C:15]([F:14])([F:25])[F:26])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 27771194-(2,2,2-Trifluoroethoxy)anilineHCID 23665647Potassium tert-butoxideHCID 866854073-Thiophenecarboxylic acid, 4-isothiocyanato-, ethyl ester

Product 1

HCID 86685406HCID 86685406, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-isothiocyanatothiophene-3-carboxylate (1.1 g) and 4-(2,2,2-trifluoroethoxy)aniline (0.99 g) were dissolved in acetonitrile (40 ml), and the solution was heated under reflux for 1 hr, and allowed to be cooled. Potassium tert-butoxide (1.27 g) was dissolved in ethanol (15 ml), and the solution was poured into the reaction mixture at room temperature. The reaction mixture was heated under reflux for 10 min, allowed to be cooled, and concentrated under reduced pressure. The obtained brown residue was dissolved in ethanol (10 ml), and the solution was poured into 0.3M hydrochloric acid (35 ml) under ice-cooling. The resulting precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran (40 ml). The solution was diluted with ethyl acetate (80 ml). This organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a solid. This solid was washed with a mixed solvent of tetrahydrofuran/isopropyl ether (1/10) to give the title compound (1.59 g) as a solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto be cooled
  4. additionthe solution was poured into the reaction mixture at room temperature
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 10 min
  7. temperatureto be cooled
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe obtained brown residue was dissolved in ethanol (10 ml)
  10. additionthe solution was poured into 0.3M hydrochloric acid (35 ml) under ice-
  11. temperaturecooling
  12. filtrationThe resulting precipitate was collected by filtration
  13. washwashed with water
  14. dissolutiondissolved in tetrahydrofuran (40 ml)
  15. additionThe solution was diluted with ethyl acetate (80 ml)
  16. dry with materialThis organic layer was dried over anhydrous magnesium sulfate
  17. customthe solvent was evaporated under reduced pressure
  18. customto give a solid
  19. washThis solid was washed with a mixed solvent of tetrahydrofuran/isopropyl ether (1/10)

Sources & evidence

ORD record
ord-3b1b2b3a535146b5b06e6b7d0ddbedd5
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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