Hydrochloric Acid → 4-Guanidinoimino-3-methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran hydrochloride

HRID 1700554Notes

Reaction equation

HRID 1700554 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=O)[CH2:8][CH:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[CH2:10][C:5]=2[O:4][CH:3]=1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl.O>C(O)C>[ClH:24].[NH:22]([N:23]=[C:7]1[C:6]2[C:2]([CH3:1])=[CH:3][O:4][C:5]=2[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:8]1)[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 183173083-Methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 1784238334-Guanidinoimino-3-methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran hydrochlorideYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.30 g), aminoguanidine hydrochloride (0.14 g), concentrated hydrochloric acid (0.062 ml), water (0.062 ml) and ethanol (30 ml) was refluxed for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol to give 4-guanidinoimino-3-methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 33) (0.30 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-d6eb0f9ebd3742929e700541482f9fea
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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