HCID 20352874, compound → HCID 20353167, compound

HRID 372035Notes

Reaction equation

HRID 372035 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13]CC3C=CC=CC=3)=[C:9]([O:21]CC3C=CC=CC=3)[CH:8]=2)[CH2:5][N:4]=[C:3]1[NH:29][C:30]([O:32][CH3:33])=[O:31]>[Pd].C(O)C.[H][H]>[CH3:1][N:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:21])[CH:8]=2)[CH2:5][N:4]=[C:3]1[NH:29][C:30]([O:32][CH3:33])=[O:31]

Participants

5

Reactant 1

HCID 20352874HCID 20352874, compound

Product 1

HCID 20353167HCID 20353167, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

This example illustrates methods according to the invention of preparing mono- and dihydroxy substituted phenyl compounds of the invention. In this example, 3.0 g. of β-methylamino-β-(3,4-dibenzyloxyphenyl)ethylamine is dissolved in 50 ml of ethanol and 2 ml of water. The solution is combined with a solution of 1.7 g of a mixture of 1-mono and 1,3-bis (methoxycarbonyl)-S-methylisothiourea in 25 ml of chloroform and allowed to stand for 8 days and then concentrated to dryness. The residue is treated with 100 ml of 0.5N hydrochloric acid and the resulting slurry is stirred vigorously in the presence of ethyl ether. Stirring is discontinued and the ether layer is removed by decantation. This process is repeated four times and the remaining aqueous slurry is then treated in the excess of saturated aqueous sodium bicarbonate solution. The product, 1-methyl-4,5-dihydro-5-(3,4-dibenzyloxyphenyl)-2-methoxycarbonylaminoimidazoline, is extracted into chloroform, the chloroform is removed and the remaining product is purified by recrystallization from 300 ml of benzene. By treating the resulting free base with a solution of 10 ml of ethanol that contains 400 mg of hydrogen chloride and then with 200 ml of ether, the hydrochloride salt is obtained. A sample of the hydrochloride salt of 1-methyl-4,5-dihydro-5-(3,4-dibenzyloxyphenyl)-2-methoxycarbonylaminoimidazole is treated according to a standard hydrogenolysis procedure using palladium-on-charcoal catalyst in ethanol and hydrogen gas at atmospheric pressure, to afford the hydrochloride salt of 1-methyl-4,5-dihydro-5-(3,4-dihydroxyphenyl)-methoxycarbonylaminoimidazole.

Sources & evidence

ORD record
ord-98adf9b3feb5446d88ba99a48c57fd2c
Source dataset
uspto-grants-1978_05
Patent number
US04088771

Reaction notes

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