Water → HCID 86635726, compound

HRID 1013336Notes

Reaction equation

HRID 1013336 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[CH:14]=[N:15][OH:16].O>CN(C=O)C>[Cl:1][C:13]1([CH:14]=[N:15][OH:16])[CH:17]=[CH:18][CH:19]=[C:11]([O:10][CH3:9])[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 293577N-[(3-Methoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 86635726HCID 86635726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimide (32.2 g, 241 mmol) was added to a solution of 3-methoxybenzaldehyde oxime (30.4 g, 201 mmol) in DMF (200 ml) at RT, causing the temperature to rise briefly to 50° C. The reaction mixture was cooled in an ice bath, stirred overnight at RT, mixed with water (250 ml) while being cooled with ice and the precipitate formed was removed by suction-filtration. The filtrate was extracted with ether (3×400 ml) and the combined organic phases were washed with water (300 ml) and sat. aq. NaCl solution (300 ml), dried and the solvent was removed under vacuum. The desired product 1-chloro-1-hydroxyiminomethyl-3-methoxybenzene was obtained as a yellowish solid (32.86 g).

Workup

  1. customto rise briefly to 50° C
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. temperaturewhile being cooled with ice
  4. customthe precipitate formed
  5. customwas removed by suction-filtration
  6. extractionThe filtrate was extracted with ether (3×400 ml)
  7. washthe combined organic phases were washed with water (300 ml) and sat. aq. NaCl solution (300 ml)
  8. customdried
  9. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c495f19d278b49c9bbdfc663450aeb6a
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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