Methanol → Ethyl 2-(2-bromophenylamino)-6-benzoxazolylacetate

HRID 1372613노트

반응식

HRID 1372613 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=S.[CH3:24]O>>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[O:1][C:2]2[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:24])=[O:11])[CH:5]=[CH:6][C:7]=2[N:8]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 6116541-Bromo-2-isothiocyanatobenzeneHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

생성물 1

HCID 58779103Ethyl 2-(2-bromophenylamino)-6-benzoxazolylacetate수율 66%

실험 절차

Methyl 3-hydroxy-4-aminophenylacetate (2.97 g, 16.4 mmol) was dissolved in methanol (30 ml). Under stirring at room temperature, 2-bromophenyl isothiocyanate (2.65 ml, 19.7 mmol) was added to the resulting solution. The reaction mixture was then stirred at room temperature for 1.5 hours. Mercuric oxide (yellow) (3.55 g, 16.4 mmol) was added to the reaction mixture, followed by heating and refluxing for 50 minutes. After cooling the reaction mixture to room temperature, the insoluble matter was filtered off through Celite under reduced pressure. The filtrate was distilled under reduced pressure to remove the solvent. The residue was then purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, ethyl 2-(2-bromophenylamino)-6-benzoxazolylacetate (3.87 g, 66%) was obtained as a colorless solid.

후처리

  1. stirringThe reaction mixture was then stirred at room temperature for 1.5 hours
  2. temperatureby heating
  3. temperaturerefluxing for 50 minutes
  4. temperatureAfter cooling the reaction mixture to room temperature
  5. filtrationthe insoluble matter was filtered off through Celite under reduced pressure
  6. distillationThe filtrate was distilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was then purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions

출처 및 근거

ORD 기록
ord-9698cbb6f9a34bcfa28b8fbd49b21255
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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