Ethyl Acetate → 2-(2,4-Dichlorophenyl)imidazo[1,2-a]pyridine

HRID 1378951노트

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HRID 1378951 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 202502,2',4'-Trichloroacetophenone2회HCID 516892Sodium Bicarbonate

생성물 1

HCID 41097072-(2,4-Dichlorophenyl)imidazo[1,2-a]pyridine수율 38.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 8.4 g (89.2 mmol) 2-aminopyridine and 20.1 g (89.9 mmol) of 2,2',4'-trichloroacetophenone in 300 ml of ethanol was heated at reflux with stirring for 14 h. At this point, another 5.0 g (22.4 mmol) of 2,2',4'-trichloroacetophenone was added and the reaction mixture heated an additional 6 h. Ethyl acetate (400 ml) and excess saturated aqueous sodium bicarbonate were slowly added. After thorough mixing, the ethyl acetate layer was separated and washed with two fold excess water, saturated brine, and dried over magnesium sulfate. Evaporating the solvent in vacuo to almost dryness gave a wet solid residue to which n-butyl chloride was added. This solid was filtered and washed thoroughly with n-butyl chloride before drying. A yield of 9.0 g of the title compound was obtained (m.p. 173°-175° C.) as a technical material which was not purified further but used directly in the next step.

후처리

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe reaction mixture heated an additional 6 h
  4. customAfter thorough mixing, the ethyl acetate layer was separated
  5. washwashed with two fold excess water, saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporating the solvent in vacuo to almost dryness
  8. customgave a wet solid residue to which n-butyl chloride
  9. additionwas added
  10. filtrationThis solid was filtered
  11. washwashed thoroughly with n-butyl chloride
  12. custombefore drying

출처 및 근거

ORD 기록
ord-8dc8ca2b8eb8470c9ddb08d3f1b179c0
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670455

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