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1,1-Dimethoxyethyl(dimethyl)amine → 3-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehyde

HRID 1267121
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HRID 1267121 반응식
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH2:11])=[O:10].CO[C:17](OC)([N:19](C)C)[CH3:18]>>[CH3:18][C:17]1[N:11]=[C:9]([C:8]2[CH:7]=[C:6]([CH:14]=[CH:13][CH:12]=2)[CH:2]=[O:3])[O:10][N:19]=1
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참가 물질

3

반응물 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 18545471HCID 18545471, 화합물

생성물 1

HCID 185455103-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehyde수율 102.7%

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온도
90 °C

실험 절차

A mixture of 3-[1,3]dioxolan-2-yl-benzamide (2.3 g) and dimethylacetamide dimethylacetal (4 g) was heated under reflux for 1 hour and then evaporated to dryness. The oily residue was dissolved in dioxane (20 mL) and hydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added and the mixture was heated at 90° C. for 2 hours. After evaporation, the residue was dissolved in toluene (100 mL) and a 1N hydrochloric acid solution (50 mL) was added and the mixture was stirred at reflux for 2 hours. After cooling at room temperature the organic phase was decanted, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.3 g) as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. dissolutionThe oily residue was dissolved in dioxane (20 mL)
  5. additionhydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added
  6. customAfter evaporation
  7. dissolutionthe residue was dissolved in toluene (100 mL)
  8. additiona 1N hydrochloric acid solution (50 mL) was added
  9. temperatureat reflux for 2 hours
  10. temperatureAfter cooling at room temperature the organic phase
  11. customwas decanted
  12. washwashed with water
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customevaporated

출처 및 근거

ORD 기록
ord-627812b91be54b5c8e9f2a7ad0539939
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06552022B1

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