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

HRID 2384335

Reaction equation

HRID 2384335 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-77e7a92fa3224dfba447ea629275f8f7
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Linked notes

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