Hydrochloric Acid → HCID 20377674, compound

HRID 1703483Notes

Reaction equation

HRID 1703483 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH3:26])[C:22]([O:24]C)=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)=[O:4].Cl>[OH-].[K+]>[C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH3:26])[C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20377695HCID 20377695, compound

Product 1

HCID 20377674HCID 20377674, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 2-{3-(5-methoxycarbonyl-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionate (36 g) in solution in a mixture of potassium hydroxide pellets (26.4 g), distilled water (160 cc) and ethanol (400 cc), is stirred for 17 hours at a temperature of about 20° C. The resulting suspension is diluted with distilled water (800 cc) and filtered. The filtrate is stirred with decolourizing charcoal (3 g) and filtered. The solution obtained is added dropwise to a 5N aqueous solution of hydrogen chloride (400 cc) cooled in an ice bath, the rate of addition being regulated in such a way that the temperature of the mixture remains below 10° C. The reaction mixture is stirred for a further hour in the ice bath, and then the resulting crystals are filtered off, washed three times with distilled water (total 150 cc), and dried in air. Crude 2-{3-(5-carboxy-thieno[2,3-b]thien-2-yl)carbonylphenyl}propionic acid (24.3 g), melting at 244° C., is thus obtained.

Workup

  1. distillationdistilled water (160 cc) and ethanol (400 cc)
  2. additionThe resulting suspension is diluted with distilled water (800 cc)
  3. filtrationfiltered
  4. stirringThe filtrate is stirred with decolourizing charcoal (3 g)
  5. filtrationfiltered
  6. customThe solution obtained
  7. temperaturecooled in an ice bath
  8. additionthe rate of addition
  9. customremains below 10° C
  10. filtrationthe resulting crystals are filtered off
  11. washwashed three times with distilled water (total 150 cc)
  12. customdried in air

Sources & evidence

ORD record
ord-d7af266380564b968af71c10cb1561ef
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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