Pyridine → Oxaprozin

HRID 1449342

반응식

HRID 1449342 반응식
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]1([C:14]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)O)=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:24]1C=CC=CC=1>>[C:8]1([C:14]2[N:24]=[C:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])[O:7][C:16]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

4

반응물 3

HCID 1049PyridineHCID 7922Succinic anhydrideHCID 8400Benzoin

생성물 1

HCID 4614Oxaprozin수율 67%

실험 절차

A 5 liter flask was set up and equipped with stirrer, thermometer, reflux condenser and nitrogen inlet. Succinic anhydride (373 grams), benzoin (531 grams) and pyridine (300 milliliters; 296 grams) were introduced. The flask was purged with nitrogen and the reaction mixture heated to 90°-95° C. The mixture was stirred for one and a half hours at this temperature. Glacial acetic acid (1300 milliliters) and ammonium acetate (385 grams) were added to the reaction mixture and the mixture reheated to 90°-95° C. Stirring was continued and this temperature was maintained for a further 2 hours. The mixture was filtered, rinsing through with glacial acetic acid (150 milliliters). Distilled water (750 milliliters) was added and the mixture reheated to 90°-95° C. before gradual cooling with stirring to 15° C. over 1 hour. After filtering and washing with a mixture of acetic acid and distilled water in a ratio of 2:1 (600 milliliters), the product was slurried with distilled water (1000 milliliters). After filtering and washing with distilled water (2×400 milliliters), the product was dried at 90°-100° C. under vacuum. 702 Grams (67% yield) of β-(4,5-diphenyloxazol-2-yl)propionic acid were obtained as a white crystalline powder, m.p. 163°-165° C. The material was investigated for quality by TLC. The product had high purity and merely showed a number of very faint trace impurities.

후처리

  1. customA 5 liter flask was set up
  2. customequipped with stirrer
  3. temperaturethermometer, reflux condenser and nitrogen inlet
  4. customThe flask was purged with nitrogen
  5. temperaturethe reaction mixture heated to 90°-95° C
  6. additionGlacial acetic acid (1300 milliliters) and ammonium acetate (385 grams) were added to the reaction mixture
  7. customreheated to 90°-95° C
  8. stirringStirring
  9. temperaturethis temperature was maintained for a further 2 hours
  10. filtrationThe mixture was filtered
  11. washrinsing through with glacial acetic acid (150 milliliters)
  12. additionDistilled water (750 milliliters) was added
  13. customreheated to 90°-95° C.
  14. temperaturebefore gradual cooling
  15. stirringwith stirring to 15° C. over 1 hour
  16. filtrationAfter filtering
  17. washwashing with a mixture of acetic acid
  18. distillationdistilled water in a ratio of 2:1 (600 milliliters)
  19. filtrationAfter filtering
  20. washwashing with distilled water (2×400 milliliters)
  21. customthe product was dried at 90°-100° C. under vacuum

출처 및 근거

ORD 기록
ord-9de7f1ee6cc74b43b872c0c3d621d914
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04190584

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