Chlorosuccinimide → (1Z)-3-chloro-4-cyano-N-hydroxy-2-methylbenzenecarboximidoyl chloride

HRID 872817Notes

Reaction equation

HRID 872817 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](/[CH:11]=[N:12]/[OH:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Cl:14]N1C(=O)CCC1=O>CN(C=O)C>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([CH:7]=[CH:6][C:3]=1[C:4]#[N:5])/[C:11](/[Cl:14])=[N:12]/[OH:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 872947342-chloro-4-[(E)-hydroxyiminomethyl]-3-methylbenzonitrile

Product 1

HCID 87294792(1Z)-3-chloro-4-cyano-N-hydroxy-2-methylbenzenecarboximidoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(E)-2-chloro-4-((hydroxyimino)methyl)-3-methylbenzonitrile (0.64 g, 3.27 mmol) was dissolved in DMF (20 ml) and cooled to 0° C. N-Chlorosuccinimide (0.48 g, 3.60 mmol) was added and the mixture was allowed to warm at RT. The mixture was stirred overnight at RT and poured into ice water (100 ml), extracted twice with EtOAc, The organic phase was washed with water and brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product (0.69 g) was used without purification. 1H-NMR (400 MHz; d6-DMSO): δ 2.42 (s, 3H), 7.64 (d, 1H), 7.92 (d, 1H), 12.77 (s, 1H).

Workup

  1. temperatureto warm at RT
  2. extractionextracted twice with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product (0.69 g) was used without purification

Sources & evidence

ORD record
ord-de5abd61ce7e4021a6c81387a93d1e86
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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