1H,3H-Thieno[3,4-c]furan-1,3-dione → HCID 58401155, compound

HRID 868789Notes

Reaction equation

HRID 868789 reaction equation
[S:1]1[CH:5]=[C:4]2[C:6](O[C:9](=[O:10])[C:3]2=[CH:2]1)=[O:7].[CH2:11]([CH:13]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:14][CH2:15][C:16]1[C:22]([F:23])=[C:21]([F:24])[C:19]([NH2:20])=[C:18]([F:25])[C:17]=1[F:26])[CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([CH:13]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:14][CH2:15][C:16]1[C:17]([F:26])=[C:18]([F:25])[C:19]([N:20]2[C:9](=[O:10])[C:3]3=[CH:2][S:1][CH:5]=[C:4]3[C:6]2=[O:7])=[C:21]([F:24])[C:22]=1[F:23])[CH3:12]

Participants

4

Reactant 2

HCID 3156081H,3H-Thieno[3,4-c]furan-1,3-dioneHCID 58401142HCID 58401142, compound

Product 1

HCID 58401155HCID 58401155, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. filtrationThe crude product is collected by filtration of the cold reaction mixture
  2. customAnother portion of product can be recovered
  3. washby washing the filtrate with 5% hydrochloric acid
  4. customevaporating the solvent
  5. customThe target molecule is purified by recrystallization from toluene
  6. dissolutiondissolved in 150 ml of thionyl chloride
  7. temperaturerefluxed for 3 hrs
  8. concentrationThe reaction mixture is concentrated down
  9. customdried
  10. custompurified

Sources & evidence

ORD record
ord-ca288ede37584a1b87b069c2f276a2c6
Source dataset
uspto-grants-2015_03
Patent number
US08968885B2

Reaction notes

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