4-Chlorobutyryl chloride → HCID 12051895, compound

HRID 2306045Notes

Reaction equation

HRID 2306045 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 20 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 (3X75 mL), combine the aqueous layers and extract with methylene chloride (2X75 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 (3X75 mL)
  6. extractionextract with methylene chloride (2X75 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-51a1c827ef1f447bb369869035083223
Source dataset
uspto-grants-2002_08
Patent number
US06441179B1

Reaction notes

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