Hydrochloric Acid → HCID 22750143, compound

HRID 972214Notes

Reaction equation

HRID 972214 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[S:12]1[CH:16]=[CH:15][C:14]2[CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][CH2:21][C:13]1=2.Cl>C(Cl)Cl>[S:12]1[C:16]([C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[CH:15][C:14]2[CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][CH2:21][C:13]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 14436812HCID 14436812, compound

Product 1

HCID 22750143HCID 22750143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

11.0 g of succinic acid anhydride are dissolved in 220 cc of anhydrous methylene chloride with heating, the resulting solution is cooled to 20° and 30 g of aluminium chloride are added portionwise. After stirring for 15 minutes at room temperature, a solution of 22.0 g of 9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene in 100 cc of anhydrous methylene chloride is added dropwise within 30 minutes, the resulting mixture is stirred for a further 45 minutes at room temperature and is poured on a mixture of 200 cc of concentrated hydrochloric acid and 200 g of ice. After adding 300 cc of methylene chloride, the entire mixture is heated for 15 minutes on a water bath, is cooled, the methylene chloride is removed and the aqueous phase is further extracted with methylene chloride. The acidic portion is extracted from the combined methylene chloride solutions with 0.5 normal caustic soda, the basic extract is acidified with 5 N hydrochloric acid and extracted with chloroform. The chloroform solutions are washed with water, dried over magnesium sulphate, filtered through active charcoal and evaporated to dryness. The title compound, obtained as solid residue, is recrystallized from dimethyl formamide/acetone. M.P. 202° to 203°.

Workup

  1. temperaturewith heating
  2. temperaturethe resulting solution is cooled to 20°
  3. stirringthe resulting mixture is stirred for a further 45 minutes at room temperature
  4. temperaturethe entire mixture is heated for 15 minutes on a water bath
  5. temperatureis cooled
  6. customthe methylene chloride is removed
  7. extractionthe aqueous phase is further extracted with methylene chloride
  8. extractionThe acidic portion is extracted from the combined methylene chloride solutions with 0.5 normal caustic soda
  9. extractionthe basic extract
  10. extractionextracted with chloroform
  11. washThe chloroform solutions are washed with water
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered through active charcoal
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-c433683faa9f46ee90801a4d521455a8
Source dataset
uspto-grants-1977_10
Patent number
US04052412

Reaction notes

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