Tetrahydrofuran → HCID 12149035, compound

HRID 1611605Notes

Reaction equation

HRID 1611605 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:18]=[CH:17][S:16][C:15]=1C(O)=O)([O-:7])=[O:6].C1[CH2:26][O:25]CC1.[N-:27]=[N+]=[N-].[Na+]>C1C=CC=CC=1.O>[N+:5]([C:8]1[C:9]2[C:14]3[CH:18]=[CH:17][S:16][C:15]=3[NH:27][C:26](=[O:25])[C:10]=2[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 12149034HCID 12149034, compound

Product 1

HCID 12149035HCID 12149035, compoundYield 2.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

2 ml of thionyl chloride were added to a solution of 3-(2-nitrophenyl)thiophen-2-carboxylic acid (9) (3.5 g, 14 mmol) in 20 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 50 ml of THF, and NaN3 (1.37 g, 21 mmol) in 10 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 100 ml of ice and water and extracted with ethyl ether (4×50 ml), the separated organic layer was dried over anhydrous sodium sulphate and leaving it for 2 hrs with stirring. It was evaporated under vacuum and coevaporated with anhydrous benzene (3×50 ml). It is evaporated and the residue was solubilized in 60 ml of o-dichlorobenzene and refluxed using a Dean-Stark apparatus. The mixture was left under reflux for 20 hrs with stirring, then cooled and evaporated. The mixture was subjected to flash chromatography, and elution with chloroform yielded the compound 9-nitrothieno-[2,3-c]-isoquinolin-5(4H)-one (0.075 g, 2.2% yield) as a yellow solid (M. Pt, 255–258° C.).

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 (4×50 ml)
  5. dry with materialthe separated organic layer was dried over anhydrous sodium sulphate
  6. customleaving it for 2 hrs
  7. stirringwith stirring
  8. customIt was evaporated under vacuum
  9. customIt is evaporated
  10. temperaturerefluxed
  11. waitThe mixture was left
  12. temperatureunder reflux for 20 hrs
  13. stirringwith stirring
  14. temperaturecooled
  15. customevaporated
  16. washThe mixture was subjected to flash chromatography, and elution with chloroform

Sources & evidence

ORD record
ord-6ee4ccc3365f4cbba00a659de9dcf084
Source dataset
uspto-grants-2006_01
Patent number
US06989388B2

Reaction notes

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