Dimethylformamide → N-isopropyl-4'-chloro-2-methylacetoacetanilide

HRID 224498Notes

Reaction equation

HRID 224498 reaction equation
[CH:1]([N:4]([C:12](=[O:17])[CH2:13][C:14]([CH3:16])=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:18]N(C)C=O.[H-].[Na+].CI>O>[CH:1]([N:4]([C:12](=[O:17])[CH:13]([CH3:18])[C:14]([CH3:16])=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20297524N-isopropyl-4'-chloroacetoacetanilide

Product 1

HCID 20297522N-isopropyl-4'-chloro-2-methylacetoacetanilideYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A one liter reaction flask equipped with a power stirrer, condener, drying tube, thermometer and nitrogen inlet tube was charged with 48.5 g (0.19 mole) of N-isopropyl-4'-chloroacetoacetanilide and 145 ml of dry dimethylformamide. With efficient stirring in a nitrogen atmosphere, portionwise addition of 7.2 g of 57% sodium hydride in mineral oil (0.17 mole) was completed in one hour (excessive foaming). Methyl iodide (24.1 g, 0.17 mole) was added dropwise and the reaction mixture was stirred for two hours at ambient temperature. The mixture was poured into one liter of cold water and stirred. The organic material was extracted into toluene and the latter was water washed. Most of the toluene was removed on the rotary evaporator. Hexane was added which caused the mass to crystallize. There was obtained 36.4 g (80%) of white material, M.P. 77°-79°. N.M.R. (CDCl3) ∂0.9-1.4 (CH3, 9 protons), 2.0 (0=C--CH3), 2.9-3.2 (CH), 4.7-5.2 (CH, isopropyl), 6.9-7.5. (aromatic).

Workup

  1. customA one liter reaction flask
  2. customequipped with a power stirrer
  3. customcondener, drying tube
  4. stirringstirred
  5. extractionThe organic material was extracted into toluene
  6. washwashed
  7. customMost of the toluene was removed on the rotary evaporator
  8. additionHexane was added which
  9. customto crystallize

Sources & evidence

ORD record
ord-6c275ddd54634c66af47631b8fef69a0
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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