Benzamide → Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate

HRID 4399

반응식

HRID 4399 반응식
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>>[C:2]1([C:1]2[O:8][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 2331BenzamideHCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium Bicarbonate

생성물 1

HCID 15567335Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate수율 38%

반응 조건

온도
120 °C

실험 절차

A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9) to yield ethyl 2-phenyl-4-oxazoleacetate as an oil (26.4 g, 28.0%). NMR (CDCl3)δ: 1.27 (3H, t, J=7 Hz), 3.68 (3H, s), 4.15 (2H, q, J=7 Hz), 7.4 (3H, m), 7.67 (1H, s), 8.0 (2H, m).

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9)

출처 및 근거

ORD 기록
ord-e63f4e4c221e4ca7857dee83451d2403
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725610

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