4-Chlorobutyryl chloride → HCID 12051895, compound

HRID 1836770Notes

Reaction equation

HRID 1836770 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][O:13][N:14]([CH3:26])[C:15](=[O:25])[C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17]>C(Cl)Cl>[CH3:12][O:13][N:14]([CH3:26])[C:15](=[O:25])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][Cl:5])=[CH:20][CH:19]=1)([CH3:24])[CH3:17]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59788661N-Methoxy-N-methyl-2-phenyl-isobutyramide

Product 1

HCID 12051895HCID 12051895, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Slurry AlCl3 (10.15 g, 76.1 mmol) and methylene chloride (45 mL) under a nitrogen atmosphere at room temperature. Add 4-chlorobutyryl chloride (4.27 mL, 38.1 mmol), stir for minutes and add, by dropwise addition over 10 minutes, a solution of 2-methyl-2-phenyl-propionic acid, N-methoxy-N-methylamide (6.58 g, 31.7 mmol) in methylene chloride (15 mL). Stir at room temperature for 45 minutes, then heat at 30-35° C. for 7 hours. Pour into ice water (150 mL) and separate the layers. Wash the aqueous layer with water (3×75 mL), combine the aqueous layers and extract with methylene chloride (2×75 mL). Combine the organic layers and dry (Na2SO4). Filter, evaporate the filtrate in vacuo and purify by silica gel chromatography (3:1 hexane/ethyl acetate) give the title compound (6.19 g, 63%) as a light yellow oil.

Workup

  1. customat room temperature
  2. additionadd, by dropwise addition over 10 minutes
  3. temperatureheat at 30-35° C. for 7 hours
  4. customseparate the layers
  5. washWash the aqueous layer with water (3×75 mL)
  6. extractionextract with methylene chloride (2×75 mL)
  7. dry with materialCombine the organic layers and dry (Na2SO4)
  8. filtrationFilter
  9. customevaporate the filtrate in vacuo
  10. custompurify by silica gel chromatography (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5f8b56fd19ee4567a6b82d60213818d6
Source dataset
uspto-grants-2004_08
Patent number
US06777555B2

Reaction notes

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