Hydrochloric Acid → 2-chloro-6-fluoro-N-hydroxybenzimidoyl chloride

HRID 434032

Reaction equation

HRID 434032 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4]=[N:5][OH:6].[Cl:12]N1C(=O)CCC1=O.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[N:5][OH:6])[Cl:12]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 31398Chlorosuccinimide2×HCID 2755782N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine

Product 1

HCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chlorideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzaldehyde oxime (5.13 g, 29.6 mmol) in DMF (50 ml) was added a portion of N-chlorosuccinimide followed by a syringe of HCl gas (5 ml from the vapors of a conc. HCl solution). The temperature increased slightly and the rest of the N-chlorosuccinimide (total of 4.07 g, 30.5 mmol) was added. After stirring at room temperature for 1 h, ice was added and the mixture was extracted twice with diethyl ether. The combined organic fractions were washed (brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexane/Et2O gradient) gave 2-chloro-6-fluorobenzoylchloride oxime (4.83 g, 78%).

Workup

  1. temperatureThe temperature increased slightly
  2. additionice was added
  3. extractionthe mixture was extracted twice with diethyl ether
  4. washThe combined organic fractions were washed (brine)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c72ccf017f6d4b39a8a8daf75103f417
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Linked notes

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