Ethanol → 5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

HRID 1354303Notes

Reaction equation

HRID 1354303 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].C(O)C.C(O[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[C:13]([C:16]#[N:17])[C:14]#[N:15])C>O>[NH2:15][C:14]1[O:3][N:2]=[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27867012-(Ethoxy-phenyl-methylene)-malononitrile

Product 1

HCID 134495675-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride was suspended in water (30 ml) and added sodium hydroxide (4.4 g, 0.11 mole), then ethanol (40 ml) followed by batchwise addition of 2-(Ethoxy-phenyl-methylene)-malononitrile(21.7 g, 0.11 mole). Heated reaction mixture to 50° C. for 2 hours. Removed ethanol under vacuum and filtered precipitate. Redissolved precipitate in 50% ethyl acetate/hexanes and chromatographed on silica gel to give 8.2 g product after removal of solvent (yield: 40%).

Workup

  1. temperatureHeated
  2. customreaction mixture to 50° C. for 2 hours
  3. filtrationRemoved ethanol under vacuum and filtered precipitate
  4. dissolutionRedissolved precipitate in 50% ethyl acetate/hexanes
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-52e32a4ac4ed437cbde1191cc61771be
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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