Thionyl Chloride → N-Methyl 4-Nitrobenzimidoyl Chloride

HRID 370913Notes

Reaction equation

HRID 370913 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.S(Cl)([Cl:16])=O>>[CH3:1][N:2]=[C:3]([Cl:16])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 347921N-Methyl-4-nitrobenzamide

Product 1

HCID 12410498N-Methyl 4-Nitrobenzimidoyl ChlorideYield 25.9%

Procedure

N-Methyl 4-nitrobenzamide (30.0 g, 167 mmole) and thionyl chloride (256 g, 2.15 mole) were heated at reflux for five hours. The excess thionyl chloride was removed at ~15 mm Hg. Xylene was added to the reaction and distilled under reduced pressure to yield a solid which was recrystallized from petroleum ether to yield 8.6 g of the title compound as a light yellow solid, m.p. 67°-73° C.

Workup

  1. temperatureat reflux for five hours
  2. customThe excess thionyl chloride was removed at ~15 mm Hg
  3. additionXylene was added to the reaction
  4. distillationdistilled under reduced pressure
  5. customto yield a solid which
  6. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-475bb957a2534f33886ec0b0ee0f4e0c
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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