Hydrochloric Acid → HCID 178470011, compound

HRID 1700575Notes

Reaction equation

HRID 1700575 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:11](=O)[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].[C:22]([NH:25][NH2:26])([NH2:24])=[NH:23].[ClH:27].Cl>C(O)C>[ClH:27].[CH2:1]([O:3][C:4]([C:6]1[C:10]2/[C:11](=[N:26]/[NH:25][C:22]([NH2:24])=[NH:23])/[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 183177573-Ethoxycarbonyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178470011HCID 178470011, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 3-ethoxycarbonyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.28 g) and aminoguanidine hydrochloride (111 mg) were ethanol (20 ml) and 6N hydrochloric acid (0.086 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)-3-ethoxycarbonyl-4-guanidinoimino-6-phenyl-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 55) (0.25 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-5542d85007e2452ca36752c82e0d5d84
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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