Hydrochloric Acid → HCID 20377677, compound

HRID 1703486Notes

Reaction equation

HRID 1703486 reaction equation
C([C:4]1[S:8][C:7]2[S:9][C:10]([C:12]([C:14]3[CH:15]=[C:16]([CH:20]([CH2:24][CH2:25][CH2:26][CH3:27])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:11][C:6]=2[CH:5]=1)(O)=O.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[S:9]1[C:7]2[S:8][CH:4]=[CH:5][C:6]=2[CH:11]=[C:10]1[C:12]([C:14]1[CH:15]=[C:16]([CH:20]([CH2:24][CH2:25][CH2:26][CH3:27])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=1)=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20377694HCID 20377694, compound

Product 1

HCID 20377677HCID 20377677, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
165 °C

Procedure

2-{3-(5-Carboxy-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}hexanoic acid (12.5 g) and copper powder (1 g) are suspended in quinoline (100 cc) and heated at 165° C. for 35 minutes. The reaction mixture is then heated to 190° C. over a period of 10 minutes, then cooled, poured into a mixture of 12N concentrated aqueous hydrochloric acid (120 cc) and distilled water (400 cc), and extracted three times with methylene chloride (total 300 cc). The combined methylene chloride phases are washed twice with a 2N aqueous solution of hydrogen chloride (total 60 cc), then three times with distilled water (total 90 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g), filtered and evaporated. Crude 2-{3-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}hexanoic acid (11.8 g) is thus obtained.

Workup

  1. temperatureThe reaction mixture is then heated to 190° C. over a period of 10 minutes
  2. temperaturecooled
  3. distillationdistilled water (400 cc)
  4. extractionextracted three times with methylene chloride (total 300 cc)
  5. washThe combined methylene chloride phases are washed twice with a 2N aqueous solution of hydrogen chloride (total 60 cc)
  6. dry with materialthree times with distilled water (total 90 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-09b018b920684a0e95361cb242187f29
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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