Water → 5-(Benzyloxy)-N-hydroxy-2-methylbenzenecarboximidoyl chloride

HRID 1486846Notes

Reaction equation

HRID 1486846 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:26])=[C:21](/[CH:23]=[N:24]/[OH:25])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN(C=O)C>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:26])=[C:21]([C:23]([Cl:1])=[N:24][OH:25])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 118292784(NE)-N-[(2-methyl-5-phenylmethoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 1317368235-(Benzyloxy)-N-hydroxy-2-methylbenzenecarboximidoyl chlorideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (3.72 g) was added in small portions to a solution of (E)-1-(5-(benzyloxy)-2-methylphenyl)-N-hydroxymethanimine (6.40 g) in DMF (60 mL) at room temperature, and the obtained mixture was stirred at room temperature for 2 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (6.05 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-96cc249d2ddd47c68bc4a7275efcaadb
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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