Diethyl phenylmalonate → HCID 178429823, compound

HRID 1851185Notes

Reaction equation

HRID 1851185 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([NH2:7])=[N:4][CH:3]=1.[C:8]1([CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N12CCCN=C1CCCCC2>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]2[N:7]=[C:20]([OH:21])[C:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:15]([OH:16])[N:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 66514Diethyl phenylmalonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3225595-methyl-1H-imidazol-2-amine

Product 1

HCID 178429823HCID 178429823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

18 g (135 mmol) 5-Methyl-1H-imidazol-2-ylamine are dissolved in 155 mL DMF and 31.8 g (135 mmol) diethyl phenylmalonate are added. After dropwise addition of 61.5 g (404 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene the reaction mixture is stirred at 100° C. for 16 h. The DMF has been removed and the darkbrown oily residue treated with 150 mL water (complete dissolution). 2M HCl (250 mL) is added at room temperature until a pH of 1. After stirring for 1 h at ice bath cooling the formed crystals are collected by filtration to yield the product (10.2 g=31%), which is used without further purification.

Workup

  1. customThe DMF has been removed
  2. additionthe darkbrown oily residue treated with 150 mL water (complete dissolution)
  3. addition2M HCl (250 mL) is added at room temperature until a pH of 1
  4. stirringAfter stirring for 1 h at ice bath
  5. temperaturecooling the formed crystals
  6. filtrationare collected by filtration
  7. customto yield the product (10.2 g=31%), which
  8. customis used without further purification

Sources & evidence

ORD record
ord-0fdf9dfa638a4654b04b0bfb422ee590
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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