Carbonic acid-guanidine (1:1) → HCID 178468831, compound

HRID 2387797Notes

Reaction equation

HRID 2387797 reaction equation
[C:1](=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[CH3:9][O:10][C:11](=[O:28])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH:19]([C:23](OCC)=[O:24])[C:20](=O)[CH3:21])[CH:13]=1>CCO>[CH2:9]([O:10][C:11](=[O:28])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]2[C:23]([OH:24])=[N:7][C:6]([NH2:8])=[N:5][C:20]=2[CH3:21])[CH:13]=1)[CH3:1]

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 23005490HCID 23005490, compound

Product 1

HCID 178468831HCID 178468831, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Guanidine carbonate (2.71 g) was added to a stirred solution of 3-(2-ethoxycarbonyl-3-oxobutyl)-benzoic acid methyl ester (2.12 g) in EtOH (40 mL). The reaction mixture was heated to reflux for 6 h and allowed to cool. The solvent was evaporated under reduced pressure and the residue suspended in water (30 mL). The resulting precipitate was collected by filtration and the solid suspended in EtOAc (30 mL). The solid was collected by filtration to give the subtitle compound as a colourless solid 2.12 g that was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureto cool
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationThe resulting precipitate was collected by filtration
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-e8372107c8424546b5ce029fae8c58d5
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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