4-Chlorobutyryl chloride → 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid dimethylamide

HRID 1018082

반응식

HRID 1018082 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][N:13]([CH3:25])[C:14](=[O:24])[C:15]([CH3:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:25][N:13]([CH3:12])[C:14](=[O:24])[C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][Cl:5])=[CH:21][CH:22]=1)([CH3:23])[CH3:16]

참가 물질

6

반응물 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 540072552-Methyl-2-phenyl-propionic acid, dimethylamide

생성물 1

HCID 120498702-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid dimethylamide수율 72.4%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매2회HCID 6344Dichloromethane용매

실험 절차

Add AlCl3 (1.12 g, 8.40 mmol) to carbon tetrachloride (6 mL) under a nitrogen atmosphere at room temperature. Add 4-chlorobutyryl chloride (0.49 mL, 4.37 mmol), stir for 15 minutes and add, by dropwise addition over 3 minutes, a solution of 2-methyl-2-phenyl-propionic acid, dimethylamide (0.64 g, 3.36 mmol) in carbon tetrachloride (6 mL). Stir at room temperature for 17 hours, dilute with methylene chloride (10 mL), pour into ice water (50 mL) and separate the layers. Wash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate, combine the organic layers and dry (Na2SO4). Filter, evaporate the filtrate in vacuo and purify by silica gel chromatography (5:2 hexane/ethyl acetate) to give the title compound (0.72 g, 72%) as a light yellow oil.

후처리

  1. additionadd, by dropwise addition over 3 minutes
  2. customseparate the layers
  3. washWash the aqueous layer with methylene chloride (2×70 mL), 5% aqueous sodium hydrogen carbonate
  4. dry with materialdry (Na2SO4)
  5. filtrationFilter
  6. customevaporate the filtrate in vacuo
  7. custompurify by silica gel chromatography (5:2 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-d5415e349d4c4510a5b5152343764241
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479663B2

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