Potassium Carbonate → 4-Chloro-N-[2-(2-methylpropoxy)phenyl]butanamide

HRID 359540Notes

Reaction equation

HRID 359540 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:8][CH:9]([CH3:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH:9]([CH3:19])[CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 13654662(2-Isobutoxyphenyl)amine

Product 1

HCID 144055174-Chloro-N-[2-(2-methylpropoxy)phenyl]butanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 44 ml of 4-chlorobutyryl chloride in 350 ml of ether is added dropwise to a suspension of 60 g of 2-(2-methylpropoxy)benzenamine and 199 g of potassium carbonate in 500 ml of ether, cooled in an icebath, and the mixture is stirred overnight at room temperature. The mixture is filtered and the filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution. The ethereal solution is dried over magnesium sulphate and the solvent evaporated off. 85.8 g of syrupy product are collected, and used without further treatment in the following stage.

Workup

  1. temperaturecooled in an icebath
  2. filtrationThe mixture is filtered
  3. washthe filtrate washed successively with 200 ml of 1 N sodium hydroxide, three times 100 ml o& water and 100 ml of saturated sodium chloride solution
  4. dry with materialThe ethereal solution is dried over magnesium sulphate
  5. customthe solvent evaporated off
  6. custom85.8 g of syrupy product are collected

Sources & evidence

ORD record
ord-ef113aab5bf34d70a9ad1a5228c15bfd
Source dataset
uspto-grants-1991_03
Patent number
US05001159

Reaction notes

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