5-(4-Nitrophenyl)-2-furancarboxylic acid → N-(3,5-di-t-butyl-4-hydroxyphenyl)-5-(4-aminophenyl)-2-furan carboxamide

HRID 1988350Notes

Reaction equation

HRID 1988350 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29]([C:31](O)=[O:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)([O-])=O.C(OC(NC1C=CC(CC(O)=O)=CC=1)=O)(C)(C)C>>[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:31]([C:29]2[O:30][C:26]([C:23]3[CH:24]=[CH:25][C:20]([NH2:17])=[CH:21][CH:22]=3)=[CH:27][CH:28]=2)=[O:32])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1615935-(4-Nitrophenyl)-2-furancarboxylic acidHCID 3142204-Amino-2,6-di-tert-butylphenolHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid

Product 1

HCID 21918733N-(3,5-di-t-butyl-4-hydroxyphenyl)-5-(4-aminophenyl)-2-furan carboxamideYield 56%

Procedure

The experimental protocol used is the same as that described for intermediate 40.1, 2,6-di-t-butyl-4-aminophenol and 5-(4-nitrophenyl)-2-furan carboxylic acid replacing thiazolidine and 4-(t-butoxycarbonylamino)-benzeneacetic acid respectively. The expected compound is obtained in the form of a colourless oil with a yield of 56%.

Sources & evidence

ORD record
ord-e9f84fffa4014509b080b96885a85768
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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