Propanoic acid, 3-iodo- → n-(2-Carboxyethyl)-2,3,3-trimethylindolinium iodide

HRID 480526

반응식

HRID 480526 반응식
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[I:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]>>[I-:13].[C:16]([CH2:15][CH2:14][NH+:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH3:12])([CH3:11])[CH:2]1[CH3:1])([OH:18])=[O:17]

참가 물질

3

반응물 2

HCID 8856Propanoic acid, 3-iodo-HCID 154273H-Indole, 2,3,3-trimethyl-

생성물 1

HCID 18764709n-(2-Carboxyethyl)-2,3,3-trimethylindolinium iodide

반응 조건

온도
80 °C

실험 절차

A 2-necked 50 milliliter round-bottomed flask equipped with a magnetic stirring bar and an argon inlet was charged with re-distilled (pressure 2 mm Hg, temperature 45° C.) 2,3,3-trimethylindolenine (7.95 grams, 50.0 mmol) and 3-iodopropionic acid (2.00 grams, 10 mmol). The mixture was heated to 80° C. for 12 hours, during which time the product precipitated out of solution and formed a highly viscous medium. Upon cooling, the reaction mixture was extracted three times with 200 milliliter portions of diethyl ether to remove all of the unreacted starting material. The remaining crystalline solid was then dissolved in 10 milliliters of water, extracted three times with 50 milliliter portions of diethyl ether, and extracted three times with 25 milliliter portions of CHCl3. The aqueous layer was then removed and dried under vacuum (1.0 mm Hg) for 24 hours. The resulting amorphous solid was then recrystallized from toluene/CHCl3 mixtures to produce the N-(2-carboxyethyl)-2,3,3-trimethylindolinium iodide product as 3.0 grams of a yellow solid (83.5 percent yield). 1H and 13C NMR spectra indicated the following:

후처리

  1. customA 2-necked 50 milliliter round-bottomed flask equipped with a magnetic stirring bar and an argon inlet
  2. additionwas charged
  3. customprecipitated out of solution
  4. customformed a highly viscous medium
  5. temperatureUpon cooling
  6. extractionthe reaction mixture was extracted three times with 200 milliliter portions of diethyl ether
  7. customto remove all of the
  8. dissolutionThe remaining crystalline solid was then dissolved in 10 milliliters of water
  9. extractionextracted three times with 50 milliliter portions of diethyl ether
  10. extractionextracted three times with 25 milliliter portions of CHCl3
  11. customThe aqueous layer was then removed
  12. customdried under vacuum (1.0 mm Hg) for 24 hours
  13. customThe resulting amorphous solid was then recrystallized from toluene/CHCl3

출처 및 근거

ORD 기록
ord-ba371696e8544745b9f7722ec2a8203e
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06652959B2

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