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

HRID 413527

Reaction equation

HRID 413527 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-498cebe4a2f544bbaeb48210327b05a4
Source dataset
uspto-grants-2003_05
Patent number
US06566526B2

Linked notes

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