4-Nitrophenol → N,N'-Dicyclohexylurea

HRID 2295368Notes

Reaction equation

HRID 2295368 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 product (0.75 g, 0.0024 mole) is dissolved in 50 ml ethyl acetate. This is cooled to -5° C. and p-nitrophenol is added followed by the portionwise addition of dicyclohexylcarbodiimide. The reaction mixture is stirred at -5° C. for 2 hours. The formed dicyclohexylurea is filtered off. After concentrating to a 10 ml volume, the reaction mixture is cooled overnight. More dicyclohexylurea is formed. This is filtered and the filtrate is concentrated in vacuo to yield 0.95 g of active ester, (the p-nitrophenyl ester of N-[N-[2-(mercaptomethyl)-4-methyl-1-oxopentyl]glycyl]glycine).

Workup

  1. filtrationThe formed dicyclohexylurea is filtered off
  2. concentrationAfter concentrating to a 10 ml volume
  3. temperaturethe reaction mixture is cooled overnight

Sources & evidence

ORD record
ord-687e8519f6564965b2c3d04bd09292b6
Source dataset
uspto-grants-1984_01
Patent number
US04424354

Reaction notes

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