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

HRID 1010834ノート

反応式

HRID 1010834 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1aa0bc934e8b447482546ca474dd12f9
出典データセット
uspto-grants-2011_07
特許番号
US07977342B2

反応ノート

読み込み中…