Malonic Acid → N,N'-Dicyclohexylurea

HRID 2380744Notes

Reaction equation

HRID 2380744 reaction equation
C(O)(=O)CC(O)=[O:4].C1(C(O)C)C=CC=CC=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>C(#N)C>[CH:26]1([NH:25][C:24]([NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:4])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 74091-PhenylethanolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Malonic acid (12 g, 0.11 mol) was dissolved in acetonitrile (450 mL) in an Erlenmeyer flask (1 L) together with 1-phenyl-ethanol (26 g, 0.22 mol). Dicyclohexylcarbodiimide (45 g) was added in portions and with cooling over 10 min so the temperature did not exceed 30° C. A precipitate of dicyclohexyl urea formed almost immediately. Stirring at RT continued over the week-end to complete the reaction. Dicyclohexyl urea was removed by filtration and the filter cake was washed with addition acetonitrile (10 mL). The combined solution was evaporated in vacuum to give the crude product as colourless oil. Yield: 29 g, 93%.

Workup

  1. temperaturewith cooling over 10 min so the temperature
  2. customdid not exceed 30° C

Sources & evidence

ORD record
ord-89c519da4006402697625f65f8045746
Source dataset
uspto-grants-2012_09
Patent number
US08257786B2

Reaction notes

Loading…