[2,2'-Bithiophene]-3,3'-dicarboxylic acid → Dithieno(3,2-c:2',3'-e)oxepine-4,6-dione

HRID 536989Notes

Reaction equation

HRID 536989 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[C:2]1[C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([OH:16])=[O:15]>C(OC(=O)C)(=O)C>[S:10]1[CH:11]=[CH:12][C:13]2[C:14]([O:16][C:6]([C:3]3[CH:4]=[CH:5][S:1][C:2]=3[C:9]1=2)=[O:8])=[O:15]

Participants

3

Reactant 1

HCID 85749631[2,2'-Bithiophene]-3,3'-dicarboxylic acid

Product 1

HCID 89807128Dithieno(3,2-c:2',3'-e)oxepine-4,6-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

Diacid (3) (12.6 g, 49.4 mmol) was stirred in 100 mL of acetic anhydride at reflux for 6 h. Upon cooling to 0° C., the solid was collected by filtration, washed with 20 mL of cold acetic anhydride, and dried in vacuo at 120° C. overnight. The resulting light yellow crystals (11.4 g, 98% yield) were used without further purification. Anal. Calcd. for C10H4O3S2: C, 50.84; H, 1.71. Found: C, 50.78; H, 1.66; 1H NMR (CDCl3): 7.68 (d, J=4.0 Hz, 2H), 7.40 (d, J=5.0 Hz, 2H); m.p. 260-263° C.; MS (EI): m/z (%) 235.96 (100) [M+].

Workup

  1. temperatureat reflux for 6 h
  2. filtrationthe solid was collected by filtration
  3. washwashed with 20 mL of cold acetic anhydride
  4. customdried in vacuo at 120° C. overnight

Sources & evidence

ORD record
ord-d22914b673df4785b27f0c170cb4a231
Source dataset
uspto-grants-2014_10
Patent number
US08859714B1

Reaction notes

Loading…