Hydrochloric Acid → HCID 15524296, compound

HRID 322229Notes

Reaction equation

HRID 322229 reaction equation
Cl.C([NH:5][C:6]1[C:11]2[C:12](=[O:20])[C:13]3[S:19][CH:18]=[CH:17][C:14]=3[CH2:15][S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1)(=O)C.C(=O)([O-])O.[Na+]>CO>[NH2:5][C:6]1[C:11]2[C:12](=[O:20])[C:13]3[S:19][CH:18]=[CH:17][C:14]=3[CH2:15][S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 155242959-Acetamido-4,10-dihydrothieno[3,2-c][1]benzothiepin-10-one

Product 1

HCID 15524296HCID 15524296, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixed solvent of methanol (15 ml) and concentrated hydrochloric acid (15 ml), 9-acetamido-4,10-dihydrothieno[3,2-c][1]benzothiepin-10-one obtained in Reference Example 4 (0.74 g, 2.5 mmol) was heated under reflux for one hour. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extraction with ethyl acetate (25 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure to give 9-amino-4,10-dihydrothieno[3,2-c][1]benzothiepin-10-one as a yellow solid (0.6 g, 99%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. extractionfollowed by extraction with ethyl acetate (25 ml)
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-12e7e31d92164f6582278df398a5a13e
Source dataset
uspto-grants-2001_04
Patent number
US06211227B1

Reaction notes

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