Ethanol → N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide

HRID 1644056

반응식

HRID 1644056 반응식
[OH-].[K+].[OH:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[O:9])=[CH:6][C:5]=1[CH3:20].Cl[CH:22]([OH:24])[CH3:23].[CH2:25](O)C>>[CH3:17][CH2:16][CH2:15][CH:11]([NH:10][C:8](=[O:9])[C:7]1[CH:18]=[CH:19][C:4]([O:3][CH2:23][CH2:22][O:24][CH3:25])=[C:5]([CH3:20])[CH:6]=1)[CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 126390351-Chloroethan-1-olHCID 575277684-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide

생성물 1

HCID 57527906N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide수율 39%

반응 조건

온도
80 °C

실험 절차

Potassium hydroxide (4 mmol) was dissolved in ethanol (5 mL) and heated at 80° C. 4-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide (example 58) (1 mmol) was added into the solution followed by chloroethanol (3 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated down and dissolved in 5% citric acid. the mixture was stirred for 1 hour. The aqueous mixture was extracted three times with ethyl acetate. The combined ethyl acetate was washed with water and dried down over sodium sulfate. The organic layer was concentrated down and purified by HPLC to yield 39% of N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide. MS (M+H, 308.25).

후처리

  1. concentrationThe reaction mixture was concentrated down
  2. dissolutiondissolved in 5% citric acid
  3. stirringthe mixture was stirred for 1 hour
  4. extractionThe aqueous mixture was extracted three times with ethyl acetate
  5. washThe combined ethyl acetate was washed with water
  6. dry with materialdried down over sodium sulfate
  7. concentrationThe organic layer was concentrated down
  8. custompurified by HPLC

출처 및 근거

ORD 기록
ord-a99ddfc8bf2a4c96918318e8b2828930
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124121B2

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