Tetrahydrofuran → Thieno(2,3-c)isoquinolin-5(4H)-one

HRID 1169624Notes

Reaction equation

HRID 1169624 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[CH:15]=[CH:14][S:13][C:12]=2C(O)=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1[CH2:23][O:22]CC1.[N-:24]=[N+]=[N-].[Na+]>C1C=CC=CC=1.O>[CH:15]1[C:11]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:23](=[O:22])[NH:24][C:12]=2[S:13][CH:14]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 25176253-phenylthiophene-2-carboxylic Acid

Product 1

HCID 9899130Thieno(2,3-c)isoquinolin-5(4H)-oneYield 44%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

0.08 ml of thionyl chloride were added to a solution of 3-phenylthiophen-2-carboxylic acid (6) (0.138 g, 0.68 mmol) in 2 ml of anhydrous benzene and the mixture was refluxed for 2 hrs. The solvent and the excess thionyl chloride were removed under vacuum and the residue was taken up using 3 ml of THF, and NaN3 (0.066 g, 1.02 mmol) in 1 ml of water was added rapidly to this stirred solution at 0° C. The mixture was left for 1 hr at room temperature with stirring, poured into 10 ml of crushed ice and water and extracted with ethyl ether (4×10 ml) and the separated organic layer was washed, dried and evaporated under vacuum. The residue was dissolved in 1 ml of o-dichlorobenzene and then added dropwise to 3 ml of boiling o-dichlorobenzene with stirring. The mixture was refluxed for 5 hrs, then cooled and evaporated. The mixture was subjected to flash chromatography, elution with 90:10 petroleum ether-ethyl acetate giving the end compound (7) (0.061 g, 0.3 mmol, 44% yield) as a pure solid (M. Pt. 266-268° C.); IR: 2849, 1647 cm−1 (NHCO).

Workup

  1. temperaturethe mixture was refluxed for 2 hrs
  2. customThe solvent and the excess thionyl chloride were removed under vacuum
  3. additionwas added rapidly to this stirred solution at 0° C
  4. extractionextracted with ethyl ether (4×10 ml)
  5. washthe separated organic layer was washed
  6. customdried
  7. customevaporated under vacuum
  8. dissolutionThe residue was dissolved in 1 ml of o-dichlorobenzene
  9. additionadded dropwise to 3 ml of boiling o-dichlorobenzene
  10. stirringwith stirring
  11. temperatureThe mixture was refluxed for 5 hrs
  12. temperaturecooled
  13. customevaporated

Sources & evidence

ORD record
ord-ef156c4af2fc4583b2ecb87915745c18
Source dataset
uspto-grants-2010_11
Patent number
US07825129B2

Reaction notes

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