N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-N'-phenylurea → HCID 20068040, compound

HRID 982492Notes

Reaction equation

HRID 982492 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]([CH2:16][OH:17])([CH2:14][OH:15])[CH2:12][OH:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]1([C:24](=[O:30])[CH2:25][C:26](OC)=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CO>[C:1]1([NH:7][C:8]([NH:10][C:11]([CH2:12][O:13][C:26](=[O:27])[CH2:25][C:24]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:30])([CH2:16][O:17][C:26](=[O:27])[CH2:25][C:24](=[O:30])[CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:14][O:15][C:26](=[O:27])[CH2:25][C:24]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:30])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3996502N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-N'-phenylureaHCID 11008598Methyl 3-cyclohexyl-3-oxopropanoate

Product 1

HCID 20068040HCID 20068040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.4 g (35 mmol) of the compound (11) and 22.0 g (119 mmol) of methyl 3-cyclohexyl-3-oxo-propionate are heated at 130° C. in a Claisen apparatus for 4 hours under application of a weak vacuum, the methyl alcohol formed being distilled off. The excess methyl 3-cyclohexyl-3-oxo-propionate (boiling point 75°-76° C./0.05 mm Hg) is then distilled off from the mixture. A brownish highly viscous oil of N-phenyl-N'-[1,1-bis-(5-cyclohexyl-3,5-dioxo-2-oxa-pentyl)-6-cyclohexyl-4,6-dioxo-3-oxa-hexyl]-urea (12) remains and can be further used without additional purification.

Workup

  1. distillationbeing distilled off
  2. distillationThe excess methyl 3-cyclohexyl-3-oxo-propionate (boiling point 75°-76° C./0.05 mm Hg) is then distilled off from the mixture
  3. customcan be further used without additional purification

Sources & evidence

ORD record
ord-2f584e52b69e40d9b4da986ca4faeb31
Source dataset
uspto-grants-1991_02
Patent number
US04996301

Reaction notes

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