Toluene → N-Ethyl-3-hydroxy-N-isopropyl-5-methylbenzamide

HRID 433961노트

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HRID 433961 반응식
[C:1]1([CH3:7])[CH:6]=[CH:5]C=CC=1.[C:8](Cl)(=[O:13])[C:9](C)([CH3:11])[CH3:10].[CH2:15]([NH:17][CH:18]([CH3:20])[CH3:19])[CH3:16].[OH-:21].[Na+]>C(N(CC)CC)C.C(O)C>[CH2:15]([N:17]([CH:18]([CH3:20])[CH3:19])[C:8](=[O:13])[C:9]1[CH:11]=[C:1]([CH3:7])[CH:6]=[C:5]([OH:21])[CH:10]=1)[CH3:16]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 88318Isopropylethylamine

생성물 1

HCID 11172073N-Ethyl-3-hydroxy-N-isopropyl-5-methylbenzamide

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8471Triethylamine용매

반응 조건

온도
2.5 °C

실험 절차

To a cooled (<5° C.) suspension of 3-hydroxy-5-methylbenzoic acid1 (50 g) in triethylamine (100 g) and toluene (500 ml) under nitrogen, was added pivaloyl chloride (97.2 ml), and the resultant mixture was stirred at 0-5° C. for 2 h. Ethylisopropylamine (55.7 ml) was added, the reaction mixture was stirred at 0-5° C. for 2 h and allowed to reach room temperature. The mixture was washed twice with water and concentrated under reduced pressure to leave a dark oil. This oil was dissolved in ethanol (500 ml) and treated with 5M NaOH solution (100 g of NaOH in 500 ml of water) for 3 h at room temperature. The ethanol was removed under reduced pressure and the resultant basic solution diluted with water and extracted with toluene. The basic layer was acidified with acetic acid to pH5 and the resultant aqueous mixture extracted with dichloromethane. The combined organic extracts were washed with brine and concentrated under reduced pressure to give the title compound as an orange/brown solid (41 g).

후처리

  1. temperatureTo a cooled
  2. customto reach room temperature
  3. washThe mixture was washed twice with water
  4. concentrationconcentrated under reduced pressure
  5. customto leave a dark oil
  6. customThe ethanol was removed under reduced pressure
  7. additionthe resultant basic solution diluted with water
  8. extractionextracted with toluene
  9. extractionthe resultant aqueous mixture extracted with dichloromethane
  10. washThe combined organic extracts were washed with brine
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bcebe37f41af4c89bc2413672c7dd1ba
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670381B2

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