4-Nitrophenol → N,N'-Dicyclohexylurea

HRID 742544Notes

Reaction equation

HRID 742544 reaction equation
N1C=CC=CC=1.C1C([N+]([O-])=[O:14])=CC=C(O)C=1.[CH:17]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCOCC1>[CH:26]1([NH:25][C:24]([NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:14])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The succinylated 2-azetidinone is dissolved in dioxane (10 ml). Anhydrous pyridine (1 ml) and p-nitrophenol (0.2 g) are added followed by dicyclohexylcarbodiimide (0.6 g, 2.5 mmole). Stirring is continued for 3 hours. The dicyclohexyl-urea formed is filtered and the filtrate is added to controlled pore glass (5 g) suspended in dimethylformamide (5 ml). Triethylamine (2 ml) is added and briefly shaken. After leaving it overnight, the CPG is filtered, washed with methanol, ether and air dried.

Sources & evidence

ORD record
ord-b862b009dea744fda672e8dd5b5650a8
Source dataset
uspto-grants-1996_09
Patent number
US05554746

Reaction notes

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