4-Nitrophenol → N,N'-Dicyclohexylurea

HRID 225107Notes

Reaction equation

HRID 225107 reaction equation
C1C([N+]([O-])=[O:8])=CC=C(O)C=1.[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(OCC)(=O)C>[C:18]([NH:17][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:8]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

The above compound (8.2 g) and p-nitrophenol (3.3 g) are dissolved in 200 ml of ethyl acetate and cooled to 5° C. N,N'-Dicyclohexylcarbodiimide (5.0 g) is added portionwise and the reaction mixture is stirred at 5° C. for about 16 hours. The dicyclohexylurea is filtered off and the ethyl acetate filtrate is concentrated in vacuo for 1 hour. Diisopropyl ether (4 ml) and ethyl acetate (4 ml) are added to the pot residue. A second crop of dicyclohexylurea is obtained. The filtrate is concentrated in vacuo to yield 8.7 g of crude active ester.

Workup

  1. filtrationThe dicyclohexylurea is filtered off
  2. concentrationthe ethyl acetate filtrate is concentrated in vacuo for 1 hour
  3. additionDiisopropyl ether (4 ml) and ethyl acetate (4 ml) are added to the pot residue

Sources & evidence

ORD record
ord-75cb159d08c54186a02900364ccd75cc
Source dataset
uspto-grants-1980_11
Patent number
US04235885

Reaction notes

Loading…