Urea → HCID 178433497, compound

HRID 1111325Notes

Reaction equation

HRID 1111325 reaction equation
[CH3:1][CH:2]([C:6](=O)[CH3:7])[C:3](=O)[CH3:4].[NH2:9][C:10]([NH2:12])=[O:11]>C(O)C.Cl>[OH:11][C:10]1[N:12]=[C:6]([CH3:7])[C:2]([CH3:1])=[C:3]([CH3:4])[N:9]=1

Participants

5

Reactant 2

HCID 1176UreaHCID 699493-Methyl-2,4-pentanedione

Product 1

HCID 178433497HCID 178433497, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To 3.65 g (32 mmol) of 3-methyl-2,4-pentanedione in ethanol (15 ml) was added urea (1.92 g; 32 mmol) followed by 3 drops concentrated HCl. This mixture was refluxed under N2 overnight (12 hours). Upon cooling a solid separated which was filtered off and washed with cold ethanol and ethyl ether. Drying on the pad gave an off-white tlc pure solid. NMR (d6 -DMSO, δ from TMS): 1.94(S, 5-CH3), 2.22(S, 4, 6 -CH3S), 5.47 (br S, OH). Mass spectroscopy showed M+ at m/e 138.

Workup

  1. temperatureThis mixture was refluxed under N2 overnight (12 hours)
  2. temperatureUpon cooling a solid
  3. customseparated which
  4. filtrationwas filtered off
  5. washwashed with cold ethanol and ethyl ether
  6. customDrying on the pad
  7. customgave an off-white tlc pure solid

Sources & evidence

ORD record
ord-403a9126e4da49afb495ed32a7c2e0e8
Source dataset
uspto-grants-1990_12
Patent number
US04980350

Reaction notes

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