Triethylamine → 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide

HRID 1250065Notes

Reaction equation

HRID 1250065 reaction equation
Cl.[N+:2]([C:5]1(OCC)[CH:10]=[CH:9][C:8](N)=[CH:7][CH2:6]1)([O-:4])=[O:3].[C:15]([C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[C:22]([OH:24])=O)([CH3:18])([CH3:17])[CH3:16].[CH2:33]([N:35](CC)CC)[CH3:34].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:30][C:29]([C:26]1[CH:25]=[C:21]([CH:20]=[C:19]([C:15]([CH3:17])([CH3:16])[CH3:18])[C:27]=1[OH:28])[C:22]([NH:35][CH2:33][CH2:34][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=1)=[O:24])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 690034264-Nitrophenetylamine hydrochloride

Product 1

HCID 219186333,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.02 g (10 mmoles) of 4-nitrophenetylamine hydrochloride, 2.5 g (10 mmoles) of 3,5-di-tert-butyl-4-hydroxy-benzoic acid, 1.38 ml (10 mmoles) of triethylamine and 2.26 g (11 mmoles) of dicyclohexylcarbodiimide are introduced into a 100 ml flask containing 20 ml of THF. The reaction medium is agitated for 15 hours at ambient temperature, the precipitate which appears is filtered out and rinsed with ethyl acetate. After concentration of the filtrate under reduced pressure, the residue is precipitated from diethyl ether. The solid is recovered by filtration and rinsed with diethyl ether. A white powder is obtained with a yield of 73%. Melting point: 204-206° C.

Workup

  1. filtrationthe precipitate which appears is filtered out
  2. washrinsed with ethyl acetate
  3. customAfter concentration of the filtrate under reduced pressure, the residue is precipitated from diethyl ether
  4. filtrationThe solid is recovered by filtration
  5. washrinsed with diethyl ether
  6. customA white powder is obtained with a yield of 73%

Sources & evidence

ORD record
ord-b58550021d6b4acc8ed9d93750a12ad9
Source dataset
uspto-grants-2002_01
Patent number
US06335445B1

Reaction notes

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