Water → 4,5-Diethyloxazol-2-amine

HRID 421029Notes

Reaction equation

HRID 421029 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 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Propioin (1.03 g, 8.37 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 a 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-dc9178b141b9494d9295114ee8c3f8ba
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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