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

HRID 1010834Notes

Reaction equation

HRID 1010834 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

Conditions

Temperature
50 °C

Procedure

Hydroxylamine hydrochloride was suspended in water (30 ml) and sodium hydroxide (4.4 g, 0.11 mole) and then ethanol (40 ml) was added, followed by batchwise addition of 2-(ethoxy-phenyl-methylene)-malononitrile (21.7 g, 0.11 mole). The reaction mixture was heated to 50° C. for 2 hours. The ethanol was removed under vacuum and the precipitate was filtered. The precipitate was redissolved in 50% ethyl acetate/hexanes and chromatographed on silica gel to give 8.2 g of product after removal of solvent (yield: 40%). The rest of the sequence was made by analogy to the methyl replacement of the phenyl analog.

Workup

  1. customThe ethanol was removed under vacuum
  2. filtrationthe precipitate was filtered
  3. dissolutionThe precipitate was redissolved in 50% ethyl acetate/hexanes
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-1aa0bc934e8b447482546ca474dd12f9
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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