Chlorosuccinimide → N-Hydroxy-2-methylbenzene-1-carboximidoyl chloride

HRID 474362

Reaction equation

HRID 474362 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14]>CN(C)C=O>[OH:14][N:13]=[C:12]([Cl:1])[C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[CH3:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1024012-Methyl-benzaldoxime

Product 1

HCID 71403975N-Hydroxy-2-methylbenzene-1-carboximidoyl chlorideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (2.22 g, 16.6 mmol, 1.0 equiv) was added to a stirred solution of 2-methyl-benzaldehyde oxime (2.25 g, 16.6 mmol, 1.0 equiv) in N,N-dimethylformamide (30 mL) at ambient temperature. Stirring was continued for 2 hours and the reaction quenched (ice-water). The resultant mixture was extracted with ethyl acetate. The combined organic extracts were washed sequentially with water (6×) and saturated aqueous sodium chloride solution (2×). The organic was then dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give 2.07 g (74%) of N-hydroxy-2-methylbenzenecarboximidoyl chloride as a green oil. 1H NMR (300 MHz, CDCl3) δ: 8.14 (s, 1H), 7.48-7.44 (m, 1H), 7.37-7.20 (m, 3H), 2.43 (s, 3H).

Workup

  1. customthe reaction quenched (ice-water)
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed sequentially with water (6×) and saturated aqueous sodium chloride solution (2×)
  4. dry with materialThe organic was then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-360efc0fbb804bd8b06eabe18bbdf9b6
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Linked notes

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