Phenol → N,N'-Dicyclohexylurea

HRID 376056Notes

Reaction equation

HRID 376056 reaction equation
[OH:1]C(P(O)O)(C)CCCC.C1(O)C=CC=CC=1.CN(C1C=CC=CN=1)C.[CH:27]1([N:33]=[C:34]=[N:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1.CCOCC>[CH:36]1([NH:35][C:34]([NH:33][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:1])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 21469992HCID 21469992, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxy-1,4-dimethylbutylphosphonous acid (0.166 g., 0.001M), phenol (0.094 g., 0.001M) and dimethylaminopyridine 0.01 g.) are stirred in tetrahydrofuran (5 ml.) at 5° C. Dicyclohexylcarbodiimide (0.23 g. 0.001M) is added portionwise over 2 hours. On completion of the reaction (31P NMR) ether (10 ml.) is added and the dicylohexyl urea formed is filtered off. Evaporation of the filtrate gives an oil which is purified on silica using 5% methanol in chloroform as eluant. There is obtained phenyl (1-hydroxy-1,4-dimethylbutyl)phosphinate.

Workup

  1. additionis added

Sources & evidence

ORD record
ord-878806209962440cab9c179ec71a16ec
Source dataset
uspto-grants-1996_01
Patent number
US05488171

Reaction notes

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