Hydrochloric Acid → HCID 19693064, compound

HRID 1832Notes

Reaction equation

HRID 1832 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[C:18](=[O:19])[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH2:12][CH2:11][C:10]=2[CH:20]=1)=O.Cl>C(O)C>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]2[C:18](=[O:19])[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH2:12][CH2:11][C:10]=2[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19693078HCID 19693078, compound

Product 1

HCID 19693064HCID 19693064, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (10 ml) was suspended 7-trimethylacetamido-4,5-dihydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophen-10-one obtained in Reference Example 17 (0.40 g, 1.28 mmol), and 6N hydrochloric acid (5 ml) was added thereto, followed by heating under reflux for 6 hours. After the reaction was completed, ethanol was distilled off under reduced pressure, and the resulting mixture was adjusted to pH 10 with an aqueous solution of sodium hydroxide. The mixture was extracted with dichloromethane, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure to give 7-amino-4,5-dihydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophen-10-one (0.29 g, 98.8%).

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 6 hours
  4. distillationethanol was distilled off under reduced pressure
  5. extractionThe mixture was extracted with dichloromethane
  6. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter the drying agent was filtered off
  9. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-26cdb6c868e440d6955dd972d622308f
Source dataset
uspto-grants-1998_03
Patent number
US05726325

Reaction notes

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