Acetonitrile → N,N-diisopropyl-2-chloro-4-fluoro-5-diacetylaminobenzylamine

HRID 231437Notes

Reaction equation

HRID 231437 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])=[CH:6][C:3]=1[CH2:4]Br.[CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C>[CH:18]([N:21]([CH2:4][C:3]1[CH:6]=[C:7]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[C:8]([F:10])=[CH:9][C:2]=1[Cl:1])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 200323672-Chloro-4-fluoro-5-diacetylaminobenzyl bromide

Product 1

HCID 20032363N,N-diisopropyl-2-chloro-4-fluoro-5-diacetylaminobenzylamineYield 95.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.82 g (0.0025 mole) of 2-chloro-4-fluoro-5-diacetylaminobenzyl bromide, 0.28 g (0.0028 mole) of diisopropylamine, 0.39 g (0.0028 mole) of potassium carbonate, and 25 ml of acetonitrile was heated at reflux overnight. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water. After being dried, the solvent was evaporated under reduced pressure, yielding 0.82 g of N,N-diisopropyl-2-chloro-4-fluoro-5-diacetylaminobenzylamine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washthe resulting mixture was washed with water
  4. customAfter being dried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6a9a2fdc57745a7b8849f59d496caed
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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