Hydrochloric Acid → 2-[(E)-[6-(4-fluorophenyl)-3-methyl-6,7-dihydro-5H-1-benzofuran-4-ylidene]amino]guanidine;hydrochloride

HRID 1700555Notes

Reaction equation

HRID 1700555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16](=O)[C:11]3[C:12]([CH3:15])=[CH:13][O:14][C:10]=3[CH2:9]2)=[CH:4][CH:3]=1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl>C(O)C>[ClH:24].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17]/[C:16](=[N:23]\[NH:22][C:19]([NH2:21])=[NH:20])/[C:11]3[C:12]([CH3:15])=[CH:13][O:14][C:10]=3[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 183176736-(4-Fluorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784311402-[(E)-[6-(4-fluorophenyl)-3-methyl-6,7-dihydro-5H-1-benzofuran-4-ylidene]amino]guanidine;hydrochlorideYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.12 g) and aminoguanidine hydrochloride (59 mg) were added ethanol (10 ml) and 6N hydrochloric acid (0.046 ml), and the mixture was stirred at 90° C. for 1 hour and cooled. The reaction solution was concentrated under reduced pressure, and the residue was washed with ethanol and isopropylether, and dried to give (E)-6-(4-fluorophenyl)-4-guanidinoimino-3-methyl-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 34) (0.12 g).

Workup

  1. temperaturecooled
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. washthe residue was washed with ethanol and isopropylether
  4. customdried

Sources & evidence

ORD record
ord-715099253734475c81e6521d85f9d913
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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