Water → 4,5-Diethyloxazol-2-amine

HRID 644394Notes

Reaction equation

HRID 644394 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH:4]([CH2:6][CH3:7])[OH:5].[N:9]#[C:10][NH2:11].[O-]CC.[Na+].O>C(O)C>[NH2:11][C:10]1[O:5][C:4]([CH2:6][CH3:7])=[C:3]([CH2:2][CH3:1])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9864CyanamideHCID 956094-Hydroxyhexan-3-oneHCID 2723922Sodium ethoxide

Product 1

HCID 178601934,5-Diethyloxazol-2-amineYield 29.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Propioin (1.03 g, 8.87 mmol) was dissolved in ethanol (15 mL). Cyanamide (0.75 g, 17.7 mmol) and sodium ethoxide (1.21 g, 17.7 mmol) were added, and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (dichloromethane:methanol=9:1) to give the title compound (369.2 mg, 29.7%) as an yellow amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-2d05618007ee46ab87577368300dfc6e
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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