Hydrochloric Acid → HCID 13934078, compound

HRID 2308999Notes

Reaction equation

HRID 2308999 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([O:12]CC)=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:24])=[O:23])=[CH:18][CH:17]=1.[OH-].[Na+].[H][H].Cl>CO>[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([OH:12])=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:15](=[O:25])[C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:24])=[O:23])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13934077HCID 13934077, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13934078HCID 13934078, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.29 g (0.0061 moles) ethyl 5,6-dihydro-2-methyl-3-(4-(methylsulfinyl) benzoyl)-4H-cyclopenta[b]thiophene-6-carboxylate, the product of Example 1a. in 40 ml of methanol at reflux was added 9.1 ml (0.0091 moles) of 1N sodium hydroxide dropwise. After 20 min. of refluxing the mixture was cooled in an ice bath and poured into 3N hydrogen chloridede dropwise. After 20 min. of refluxing the mixture was cooled in an ice bath and poured into 3N hydrogen chloride and ice. Solid 5,6-dihydro-2-methyl-3-[4-(methylsulfinyl) benzoyl]-4H-cyclopenta[b]thiophene-6-carboxylic acid was collected. The filtrate was extracted with chloroform, washed with brine and dried (MgSO4). Evaporation of the solvent gave solid acid which was recrystallized from acetonitrile. The two batches of solid were combined and recrystallized from acetonitrile to give 1.45 g of 5,6-dihydro-2-methyl-3-(4(methylsulfinyl)benzoyl)-4H-cyclopenta[b]thiophene-6-carboxylic acid, mp 209-213° C.

Workup

  1. temperatureAfter 20 min. of refluxing the mixture
  2. temperaturewas cooled in an ice bath
  3. temperatureAfter 20 min. of refluxing the mixture
  4. temperaturewas cooled in an ice bath
  5. customSolid 5,6-dihydro-2-methyl-3-[4-(methylsulfinyl) benzoyl]-4H-cyclopenta[b]thiophene-6-carboxylic acid was collected
  6. extractionThe filtrate was extracted with chloroform
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customEvaporation of the solvent
  10. customgave solid acid which
  11. customwas recrystallized from acetonitrile
  12. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-51cd892fa0ec400daca549354e1536e8
Source dataset
uspto-grants-1987_09
Patent number
US04692460

Reaction notes

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