Phenol → N,N'-Dicyclohexylurea

HRID 854221Notes

Reaction equation

HRID 854221 reaction equation
C1([OH:7])C=CC=CC=1.[CH:8]1([N:14]=[C:15]=[N:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH:17]1([NH:16][C:15]([NH:14][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:7])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 755674-Pyrrolidinopyridine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the alcohol or phenol (1.0 eq.), of the carboxylic acid (1.1 eq.), of N,N′-dicyclohexylcarbodiimide (Aldrich, purity 99%; about 1.1-1.7 eq.) and catalytic amounts of 4-pyrrolidinopyridine (Aldrich, purity 98%; about 0.01 eq.) is stirred in anhydrous dichloromethane until the reaction is complete. The N,N′-dicyclohexylurea formed is filtered off, the solvent is removed under reduced pressure, and the residue is purified as described.

Sources & evidence

ORD record
ord-2baab0ab6f5f4f88bbe6d6dd0155a727
Source dataset
uspto-grants-2007_08
Patent number
US07258902B2

Reaction notes

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