HCID 18536675, compound → HCID 18536678, compound

HRID 412046Notes

Reaction equation

HRID 412046 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5](=O)[CH:6]([CH3:10])[C:7](=O)[CH3:8])[CH3:2].C(=O)(O)[O-].[C:19]1([NH:25][C:26]([NH2:28])=[NH2+:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:10][C:6]1[C:5]([CH:4]([O:12][CH2:13][CH3:14])[O:3][CH2:1][CH3:2])=[N:27][C:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:28][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 18536675HCID 18536675, compoundHCID 178512436HCID 178512436, compound

Product 1

HCID 18536678HCID 18536678, compoundYield 114.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 44 g (purity about 50%, about 0.11 mol) of 1,1-diethoxy-3-methylpentane-2,4-dione (crude product, Example 2a) and 35 g (0.175 mol) of phenylguanidinium bicarbonate in 300 ml of ethanol was heated at 70-80° C. for about 3 hours. The reaction mixture was then concentrated and the residue was filtered, with suction, through silica gel using methyl tert-butyl ether. The solvent was evaporated. Less volatile components were distilled off under a pressure of 0.3 mbar, at a bath temperature of 150° C. The residue obtained was 38 g (quantitative yield) of the title compound as a yellow oil.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. filtrationthe residue was filtered, with suction, through silica gel
  3. customThe solvent was evaporated
  4. distillationLess volatile components were distilled off under a pressure of 0.3 mbar, at a bath temperature of 150° C
  5. customThe residue obtained

Sources & evidence

ORD record
ord-f34b6f5bfc144fff828b8d7d3e3917ff
Source dataset
uspto-grants-2003_05
Patent number
US06562833B1

Reaction notes

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