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

HRID 62014Notes

Reaction equation

HRID 62014 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 (0.28 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-ae1719c0be7943d484586798cdb9d41f
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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