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

HRID 42669Notes

Reaction equation

HRID 42669 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-3428ed0435dc43c99212754307b4a75f
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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