HCID 19759872, compound → HCID 19759867, compound

HRID 1586866Notes

Reaction equation

HRID 1586866 reaction equation
[S:1]1[C:5]2[S:6](=[O:10])(=[O:9])[CH2:7][CH2:8][C:4]=2[CH:3]=[C:2]1C(O)=O>N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C.[Cu]>[S:6]1(=[O:10])(=[O:9])[C:5]2[S:1][CH:2]=[CH:3][C:4]=2[CH2:8][CH2:7]1

Participants

5

Reactant 1

HCID 19759872HCID 19759872, compound

Product 1

HCID 19759867HCID 19759867, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

Copper dust (13.4 g. 0.20 mol) was added to a solution of 4,5-dihydrothieno[2,3-b]thiophene-2-carboxylic acid-6,6-dioxide (45 g, 0.20 mol) in quinoline (500 mL) in a reaction vessel fitted with an efficient condenser. The well stirred reaction mixture was heated to 180° C. for 1.5 hours under a nitrogen atmosphere. The dark solution was cooled to room temperature and diluted with ethyl acetate (2 L). The solution was washed with 6N HCl, water, saturated sodium bicarbonate, and saturated brine. The organic phase was dried over magnesium sulfate and treated with decolorizing carbon. Filtration and evaporation of solvent gave the title compound as a solid (33 g, 95%).

Workup

  1. customfitted with an efficient condenser
  2. customreaction mixture
  3. temperatureThe dark solution was cooled to room temperature
  4. washThe solution was washed with 6N HCl, water, saturated sodium bicarbonate, and saturated brine
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. additiontreated with decolorizing carbon
  7. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-ed5898c3547d47aabaea662bad97657c
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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