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

HRID 433961ノート

反応式

HRID 433961 の反応式
[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]

参加物

7

反応物 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 88318Isopropylethylamine

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8471Triethylamine溶媒

反応条件

温度
2.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bcebe37f41af4c89bc2413672c7dd1ba
出典データセット
uspto-grants-2003_12
特許番号
US06670381B2

反応ノート

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