Hydrochloric Acid → HCID 18422308, compound

HRID 1281896Notes

Reaction equation

HRID 1281896 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=1[NH:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[C:20](OCC)=[O:21].Cl>COCCOC>[CH:19]1[C:13]2[C:12]3[C:20](=[O:21])[NH:7][C:8]4[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=4[NH:10][C:11]=3[S:15][C:14]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18422339HCID 18422339, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 18422308HCID 18422308, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Potassium tert-butoxide (718 mg) was suspended in 1,2-dimethoxyethane (35 ml) and the mixture was refluxed under heating. Thereto was added dropwise ethyl 2-(2-aminoanilino)benzo[b]thiophene-3-carboxylate (1.0 g) dissolved in 1,2-dimethoxyethane (35 ml) over 15 minutes. After 30 minutes, potassium tert-butoxide (359 mg) was added and the mixture was refluxed under heating for 1 hour. After the completion of the reaction, the reaction mixture was allowed to cool to room temperature and poured into 0.5N hydrochloric acid. The mixed solution was extracted 3 times with chloroform, and washed with water and dried over magnesium sulfate. The solution was filtered and the solvent was evaporated under reduced pressure. The precipitated crude crystals were washed with ethyl acetate and diisopropyl ether to give 6H-[1]benzothieno[2,3-b][1,5]benzodiazepin-12(11H)-one (300 mg).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 1 hour
  5. customAfter the completion of the reaction
  6. extractionThe mixed solution was extracted 3 times with chloroform
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe solution was filtered
  10. customthe solvent was evaporated under reduced pressure
  11. customThe precipitated crude crystals
  12. washwere washed with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-42caf3ff6bab47e3a2e7cd965bbe34cb
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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