Acetanilide, 2-bromo-N-methyl- → HCID 14855467, compound

HRID 477391Notes

Reaction equation

HRID 477391 reaction equation
[Na].[F:2][C:3]([F:14])([C:8]1[CH:12]=[C:11]([OH:13])[O:10][N:9]=1)[C:4]([F:7])([F:6])[F:5].[CH3:15][N:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17](=[O:20])[CH2:18]Br>C(#N)C>[CH3:15][N:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17](=[O:20])[CH2:18][O:13][C:11]1[O:10][N:9]=[C:8]([C:3]([F:2])([F:14])[C:4]([F:7])([F:6])[F:5])[CH:12]=1

Participants

4

Reactant 2

HCID 34495Acetanilide, 2-bromo-N-methyl-HCID 178516125HCID 178516125, compound

Product 1

HCID 14855467HCID 14855467, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To 0.50 g (2.2 mmole) of 3-pentafluoroethyl-5-hydroxyisoxazole sodium salt were added dry acetonitrile (7 ml) and N-methyl-N-phenyl-2-bromoacetamide (0.55 g) and the resulting mixture was stirred at 60° C. for 24 hours. After completion of reaction, the reaction solution was evaporated under reduced pressure and to the residue was added water (80 ml), extracted with methylene chloride, treated with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give 0.52 g of crystals. These crystals were recrystallized from n-hexane to give 0.48 g of the titled compound as colorless plates, yield 62.3%, m.p. 88.0-89.0° C.

Workup

  1. customAfter completion of reaction
  2. customthe reaction solution was evaporated under reduced pressure and to the residue
  3. additionwas added water (80 ml)
  4. extractionextracted with methylene chloride
  5. additiontreated with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ebc78d76f1ca42829655549d9ef96307
Source dataset
uspto-grants-1989_12
Patent number
US04888044

Reaction notes

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