4-Chlorobutyryl chloride → [4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

HRID 1581846Notes

Reaction equation

HRID 1581846 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][O:13][N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:15]([N:14]([O:13][CH3:12])[CH3:24])=[O:23])=[CH:22][CH:21]=1)=[O:10]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10419762N-Methoxy-N-methyl-2-phenylacetamide

Product 1

HCID 9857023[4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool a slurry of aluminum chloride (87 g, 650 mmol) in methylene chloride (100 mL) with an ice bath. Add 4-chlorobutyryl chloride (51 g, 360 mL) dropwise over 0.5 hours. Add N-methoxy-N-methyl-benzeneacetamide (53 g, 300 mmol) over 0.5 hours. Allow the resultant solution to warm to room temperature. Then heat at reflux for 6 hours. Cool the solution to room temperature. Pour the solution into ice (1L) do and add methylene chloride (1 L). Separate the organic phase. Extract the aqueous phase with methylene chloride (2×500 mL). Dry the combined organics over anhydrous magnesium sulfate and concentrate to provide a solid which contains a ca. 1:1 mixture of the title compound and the meta isomer.

Workup

  1. temperatureThen heat
  2. temperatureat reflux for 6 hours
  3. customSeparate the organic phase
  4. extractionExtract the aqueous phase with methylene chloride (2×500 mL)
  5. dry with materialDry the combined organics over anhydrous magnesium sulfate
  6. concentrationconcentrate
  7. customto provide a solid which

Sources & evidence

ORD record
ord-e8d8571660e0461ca2e1fb3c3f89344e
Source dataset
uspto-grants-2004_05
Patent number
US06730791B2

Reaction notes

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