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

HRID 1700567Notes

Reaction equation

HRID 1700567 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:15][C:14](=O)[C:9]2[C:10]([CH3:13])=[CH:11][O:12][C:8]=2[CH2:7]1.[C:17]([NH:20][NH2:21])([NH2:19])=[NH:18].[ClH:22].Cl>C(O)C>[ClH:22].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:15]/[C:14](=[N:21]\[NH:20][C:17]([NH2:19])=[NH:18])/[C:9]2[C:10]([CH3:13])=[CH:11][O:12][C:8]=2[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 183174076-(2-Furyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784311432-[(E)-[6-(furan-2-yl)-3-methyl-6,7-dihydro-5H-1-benzofuran-4-ylidene]amino]guanidine;hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-(2-furyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.22 g) and aminoguanidine hydrochloride (113 mg) were ethanol (20 ml) and 6N hydrochloric acid (0.088 ml), and the mixture was stirred at 90° C. for 2 hours and cooled. The reaction solution was concentrated under reduced pressure, and the residue was washed with ethanol, ethyl acetate and isopropylether, and dried to give (E)-6-(2-furyl)-4-guanidinoimino-3-methyl-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 47) (0.22 g).

Workup

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

Sources & evidence

ORD record
ord-9f57786235264c1ba6fd721005069136
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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