4-Nitrobenzylamine → 1-(4-Aminobenzyl)-3-(4-t-butylbenzyl)thiourea

HRID 656275Notes

Reaction equation

[C:1]([C:5]1[CH:14]=[CH:13][C:8]([CH2:9][N:10]=[C:11]=[S:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1)([O-])=O>ClCCl>[NH2:15][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:11]([NH:10][CH2:9][C:8]2[CH:13]=[CH:14][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)=[S:12])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-t-Butylbenzylisothiocyanate (100 mg) was dissolved in dichloromethane (3 ml) and then cooled to 0° C. To the solution was added 4-nitrobenzylamine (75 mg), followed by stirring at room temperature for 6 hours. After the completion of the reaction, dichloromethane was evaporated therefrom under reduced pressure and the residue was dissolved in methanol (3 ml). To the solution was added catalytic amount of 5% platinum/carbon and the mixture was subjected to hydrogenation reaction under atmospheric pressure. After the completion of the reaction, the methanol was evaporated under reduced pressure and the obtained residue was column-chromatographed (hexane/ethyl acetate=1/1) to yield the compound 9a (137 mg, 85%) as a white solid.

Workup

customwas evaporated
dissolutionunder reduced pressure and the residue was dissolved in methanol (3 ml)
additionTo the solution was added catalytic amount of 5% platinum/carbon
customthe mixture was subjected to hydrogenation reaction under atmospheric pressure
customAfter the completion of the reaction
customthe methanol was evaporated under reduced pressure
customthe obtained residue was column-chromatographed (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-86c8e660fc68438fb297733f359f023a
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071650B2

Reaction notes

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