Réaction #955971

ord-ca288ede37584a1b87b069c2f276a2c6

Équation de réaction

O=C1OC(=O)c2cscc21
thiophene-3,4-dicarboxylic anhydride
CCCCC(CC)CCc1c(F)c(F)c(N)c(F)c1F
4-(3-ethylheptyl)-2,3,5,6-tetrafluoroaniline
CCCCC(CC)CCc1c(F)c(F)c(N2C(=O)c3cscc3C2=O)c(F)c1F
5-(4-(3-ethylheptyl)-2,3,5,6-tetrafluorophenyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe crude product is collected by filtration of the cold reaction mixture
  2. 2
    AutreAnother portion of product can be recovered
  3. 3
    Lavageby washing the filtrate with 5% hydrochloric acid
  4. 4
    Autreevaporating the solvent
  5. 5
    AutreThe target molecule is purified by recrystallization from toluene
  6. 6
    workup.DISSOLUTIONdissolved in 150 ml of thionyl chloride
  7. 7
    Températurerefluxed for 3 hrs
  8. 8
    ConcentrationThe reaction mixture is concentrated down
  9. 9
    Autredried
  10. 10
    Autrepurified

Mode opératoire

A solution of thiophene-3,4-dicarboxylic anhydride (8.0 mmol) and 4-(3-ethylheptyl)-2,3,5,6-tetrafluoroaniline (8.5 mmol) in 125 ml of toluene is refluxed for 24 h. The crude product is collected by filtration of the cold reaction mixture. Another portion of product can be recovered by washing the filtrate with 5% hydrochloric acid and then evaporating the solvent. The target molecule is purified by recrystallization from toluene, dissolved in 150 ml of thionyl chloride and refluxed for 3 hrs. The reaction mixture is concentrated down, dried, and purified.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08968885B2uspto-grants-2015_03