Phosphorus pentachloride → 3,4-Dimethoxy-N-methyl-5-nitro-benzimidoyl chloride

HRID 1401305Notes

Reaction equation

HRID 1401305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[C:12]=1[O:13][CH3:14])[C:6]([NH:8][CH3:9])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[C:12]=1[O:13][CH3:14])[C:6]([Cl:19])=[N:8][CH3:9]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 670370593,4-Dimethoxy-N-methyl-5-nitrobenzamide

Product 1

HCID 866431073,4-Dimethoxy-N-methyl-5-nitro-benzimidoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 3,4-dimethoxy-N-methyl-5-nitro-benzamide (0.40 g, 1.66 mmol) in toluene (10 mL) was added phosphorous pentachloride (0.38 g, 1.83 mmol) portionwise. Upon completion of addition, the reaction mixture was warmed to reflux till complete disappearance of starting material. Evaporation to dryness resulted in a crude solid that was washed with diethyl ether, affording 3,4-dimethoxy-N-methyl-5-nitro-benzimidoyl chloride, 0.37 g (85%).

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux till complete disappearance of starting material
  4. customEvaporation to dryness
  5. customresulted in a crude solid
  6. washthat was washed with diethyl ether

Sources & evidence

ORD record
ord-a7ff8d3ff2174289a363707e0af547ff
Source dataset
uspto-grants-2014_12
Patent number
US08907099B2

Reaction notes

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