2-Aminophenol → N,N'-Dicyclohexylurea

HRID 1197084Notes

Reaction equation

HRID 1197084 reaction equation
C([O:8]C1C=CC(C(O)=O)=CC=1)CCCCCC.ON1C2C=CC=CC=2N=N1.[CH:28]1([N:34]=[C:35]=[N:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.NC1C=CC=CC=1O>O1CCCC1>[CH:37]1([NH:36][C:35]([NH:34][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)=[O:8])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 85154p-Heptoxybenzoic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4.7 g of p-heptyloxybenzoic acid, 2.7 g of 1-hydroxybenztriazole (HOBT) and 50 ml of tetrahydrofuran was added 4.2 g of dicyclohexylcarbodiimide (DCC) under ice cooling. After stirring at room temperature for 1 hour, 9 g of o-aminophenol was added to the mixture. The resulting mixture was stirred at room temperature overnight. Dicyclohexyl urea formed was filtered off and the filtrate was concentrated. The residue was dissolved in 500 ml of ethyl acetate. The solution was washed subsequently with diluted hydrochloric acid, a diluted sodium hydrogen carbonate solution and then water, dried over anhydrous magnesium sulfate and the concentrated under reduced pressure. The residue was applied to silica gel column chromatography (using 500 ml of silica gel), eluted with a toluene-ethyl acetate (1:1) mixture and further recrystallized from ethanol to obtain 5.6 g of p-heptyloxy-N-(o-hydroxyphenyl benzamide.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-32a5ddff432c4d37b20140d5f6cfcd40
Source dataset
uspto-grants-1992_05
Patent number
US05116853

Reaction notes

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