Potassium Carbonate → 1-Oxo-2,3-dihydro-1H-indene-4-carboximidamide hydrochloride

HRID 1684330Notes

Reaction equation

HRID 1684330 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[C:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])(=S)[NH2:14].C(=O)([O-])[O-].[K+].[K+].[Cl-:32].[NH4+:33]>C(Cl)Cl.O>[ClH:32].[C:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])(=[NH:33])[NH2:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2723982Triethyloxonium tetrafluoroborateHCID 14950598HCID 14950598, compound

Product 1

HCID 189379431-Oxo-2,3-dihydro-1H-indene-4-carboximidamide hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

10.8 g (54 mmol) of triethyloxonium tetrafluoroborate are added at room temperature under argon to a solution of 9.8 g (51.3 mmol) of 4-thiocarbamoyl-1-indanone in 500 ml of absolute methylene chloride. After 16 hours a mixture of 4.2 g of potassium carbonate and 4.2 ml of water is added to the reaction solution. The mixture is then stirred briefly and filtered, and the filtrate is washed with water. The organic phase is dried over magnesium sulfate, filtered and concentrated by evaporation. The resulting crude ethylthioimino ether is dissolved in 160 ml of absolute ethanol: 3.3 g (60 mmol) of ammonium chloride are added and the mixture is heated at reflux for 20 hours. After cooling, the reaction mixture is concentrated to dryness by evaporation. Starting compound (b) is purified by chromatogaphy on 1000 ml of Amberlite® ER-180 resin (water as eluant) and recrystallised from ethanol/ether, m.p. 215°-218° (decomp.).

Workup

  1. additionis added to the reaction solution
  2. filtrationfiltered
  3. washthe filtrate is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. dissolutionThe resulting crude ethylthioimino ether is dissolved in 160 ml of absolute ethanol
  8. temperaturethe mixture is heated
  9. temperatureat reflux for 20 hours
  10. temperatureAfter cooling
  11. concentrationthe reaction mixture is concentrated to dryness by evaporation
  12. customStarting compound (b) is purified by chromatogaphy on 1000 ml of Amberlite®
  13. customresin (water as eluant) and recrystallised from ethanol/ether, m.p. 215°-218° (decomp.)

Sources & evidence

ORD record
ord-f2480298dc434ffc9936466ee7ad10e7
Source dataset
uspto-grants-1997_06
Patent number
US05639911

Reaction notes

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