4-Aminobenzoic Acid → HCID 67079226, compound

HRID 338616Notes

Reaction equation

HRID 338616 reaction equation
[CH:1]1N=C[N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[N+:13]([C:16]1[CH:23]=[CH:22]C(CN)=[CH:18][CH:17]=1)([O-:15])=[O:14].NC1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1>[OH-].[Na+]>[N+:13]([C:16]1[CH:17]=[CH:18][C:10]([CH2:9][NH:8][C:6](=[O:7])[NH:3][CH2:2][C:1]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)=[CH:22][CH:23]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 291474-NitrobenzylamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 67079226HCID 67079226, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N,N-carbonyldiimidazole (1.62 g, 10 mmol), 4-nitrobenzyl amine (1.52 g, 10 mmol), p-aminobenzoic acid (1.52 g, 10 mmol), and 10 ml of 1 mol/L sodium hydroxide solution are used according to the method for the production of compound III in Method two to obtain 2.49 g of 4-[(4-nitrobenzylureido)methyl]benzoic acid (intermediate M-36) as a yellow solid, with a yield of 75.4%.

Sources & evidence

ORD record
ord-e316a2459be54063bf82a771cc3ab76a
Source dataset
uspto-grants-2014_11
Patent number
US08889876B2

Reaction notes

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