3-Nitrobenzamide → 3-Nitrobenzylamine

HRID 492033

반응식

HRID 492033 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=O)([O-:3])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][NH2:9])[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

참가 물질

3

반응물 2

HCID 125763-NitrobenzamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 1227223-Nitrobenzylamine

실험 절차

Commercially available 3-nitrobenzamide is reduced with LAH under standard conditions to afford (3-nitrophenyl)methanamine, which is reacted with N-4-methoxybenzylsulfamic acid and EDC to afford 1-(4-methoxybenzyl)-3-benzylsulfonylurea. This material is reacted with oxalyl chloride to afford 1-(3-nitrobenzyl)-3-(4-methoxybenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione whose nitro group is reduced and oxidized to afford 1-(3-hydrazinylbenzyl)-3-(4-methoxybenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione. This material is deprotected with TFA under standard conditions to afford the title compound 1-(3-hydrazinylbenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione.

출처 및 근거

ORD 기록
ord-c1ca399a72084e23b398431214e6e100
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531566B2

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