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

HRID 1010834노트

반응식

HRID 1010834 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1aa0bc934e8b447482546ca474dd12f9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977342B2

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