Dibutylamine → N,N-di-n-butyl-3,5-di-t-butyl-4-hydroxybenzamide

HRID 1282878Notes

Reaction equation

HRID 1282878 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([NH:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:19]([N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[C:8](=[O:10])[C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:13]([OH:14])=[C:12]([C:15]([CH3:16])([CH3:18])[CH3:17])[CH:11]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

Product 1

HCID 21520376N,N-di-n-butyl-3,5-di-t-butyl-4-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 25 grams (0.1 mole) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 12.9 grams (0.1 mole) of di-n-butylamine in 100 milliliters of dry tetrahydrofuran was added dropwise a solution of 20.6 grams (0.1 mole) of dicyclohexylcarbodiimide in 75 milliliters of dry tetrahydrofuran. The mixture was stirred for several hours and the white solid (dicyclohexyl urea) was filtered off and discarded. Evaporation of the filtrate gave a white solid, which was recrystallized from 1:1 benzene-hexane to give N,N-di-n-butyl-3,5-di-t-butyl-4-hydroxybenzamide; melting point 94°-95°C. When tested by the procedure of Example 2, the sample containing this compound lasted 1000 hours, about 3.3 times as long as the control.

Workup

  1. filtrationthe white solid (dicyclohexyl urea) was filtered off
  2. customEvaporation of the filtrate
  3. customgave a white solid, which
  4. customwas recrystallized from 1:1 benzene-hexane

Sources & evidence

ORD record
ord-df33b46573a4459b87aa5f0b149eeeab
Source dataset
uspto-grants-1976_08
Patent number
US03972927

Reaction notes

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