Water → 4,5-Diethyloxazol-2-amine

HRID 2384332Notes

Reaction equation

HRID 2384332 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 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-38592812edea4c74b8d0d1f47fbd0ee6
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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