Chlorosuccinimide → (Z)-N-Hydroxy-3-methyl-4-nitrobenzene-1-carbonimidoyl chloride

HRID 75799Notes

Reaction equation

HRID 75799 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])/[CH:5]=[N:6]/[OH:7].[Cl:14]N1C(=O)CCC1=O>CN(C)C=O>[OH:7]/[N:6]=[C:5](\[Cl:14])/[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59034617HCID 59034617, compound

Product 1

HCID 23159814(Z)-N-Hydroxy-3-methyl-4-nitrobenzene-1-carbonimidoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-methyl-4-nitrobenzaldehyde oxime (1.0 equiv.) in dimethylformamide, N-chlorosuccinimide (1.2 equiv.) was added in 3 portions over the period of 1 hr and the reaction mixture was stirred at r.t. for 5 hours. DMF was evaporated and the residue was diluted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether (60-80), to provide the title compound as a creamish solid (78%); 1H NMR (300 MHz, DMSO-d6) δ: 2.55 (s, 3H), 7.81-7.84 (d, J=8.7 Hz, 2H), 7.86 (s, 1H), 8.04-8.07 (d, J=8.4 Hz, 1H), 12.86 (s, 1H); IR (KBr) 3320, 3105, 2925, 1607, 1583, 1521, 1440, 1387, 1358, 1310, 1259, 1183, 1010, 860 cm−1.

Workup

  1. customDMF was evaporated
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with 5% ethyl acetate in petroleum ether (60-80)

Sources & evidence

ORD record
ord-aca26d5ffd1c46d49e65854a92e50945
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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