4-Nitroaniline → Benzamide, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-

HRID 1356397Notes

Reaction equation

HRID 1356397 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:18](O)=[O:19])([CH3:14])([CH3:13])[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:28][C:25]([C:22]1[CH:21]=[C:17]([CH:16]=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:23]=1[OH:24])[C:18]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:19])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

Product 1

HCID 7124367Benzamide, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-Yield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.38 g (10 mmoles) of 4-nitroaniline, 2.5 g (10 mmoles) of 3,5-di-tert-butyl-4-hydroxybenzoic acid and 2.26 g (11 mmoles) of dicyclohexylcarbodiimide are introduced into a 250 ml flask containing 20 ml of THF. The reaction medium is agitated for 15 hours at ambient temperature, and the precipitate which appears is filtered out and rinsed with ethyl acetate After the solution is concentrated under reduced pressure, the residue is diluted in 20 ml of ethyl acetate and the insoluble part is filtered out. The solvent is eliminated under vacuum and the residue is precipitated from diethyl ether. The solid is recovered by filtration, rinsed abundantly with diethyl ether in order to produce a white powder with a yield of 65%. Melting point: 277-278° C.

Workup

  1. filtrationthe precipitate which appears is filtered out
  2. washrinsed with ethyl acetate After the solution
  3. concentrationis concentrated under reduced pressure
  4. additionthe residue is diluted in 20 ml of ethyl acetate
  5. filtrationthe insoluble part is filtered out
  6. customthe residue is precipitated from diethyl ether
  7. filtrationThe solid is recovered by filtration
  8. washrinsed abundantly with diethyl ether in order
  9. customto produce a white powder with a yield of 65%

Sources & evidence

ORD record
ord-54da71cd539647308ba48443df69c69c
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Reaction notes

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