Water → 2-Amino-4,5-bis(furan-2-yl)oxazole

HRID 421032

Reaction equation

HRID 421032 reaction equation
[CH:1]1[CH:5]=[C:4]([CH:6]([OH:14])[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)=O)[O:3][CH:2]=1.[N:15]#[C:16][NH2:17].[O-]CC.[Na+].O>C(O)C>[NH2:17][C:16]1[O:14][C:6]([C:4]2[O:3][CH:2]=[CH:1][CH:5]=2)=[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9864CyanamideHCID 11100FuroinHCID 2723922Sodium ethoxide

Product 1

HCID 126152352-Amino-4,5-bis(furan-2-yl)oxazoleYield 31.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Furoin (0.50 g, 2.60 mmol) was dissolved in ethanol (15 mL). Cyanamide (218.8 mg, 5.20 mmol) and sodium ethoxide (530.8 mg, 7.80 mmol) were added, and the mixture was stirred at room temperature for 2 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 (hexane:ethyl acetate=1:1→1:2) to give the title compound (175.0 mg, 31.1%) as a dark brown crystal.

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 (hexane:ethyl acetate=1:1→1:2)

Sources & evidence

ORD record
ord-ab0765434ba74cbdb554c4afadea7153
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Linked notes

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