HCID 70563300, compound → HCID 70563951, compound

HRID 848667Notes

Reaction equation

HRID 848667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH2:16])=O)[C:5]([CH2:11][O:12][CH3:13])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]#[N:16])[C:5]([CH2:11][O:12][CH3:13])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 1

HCID 70563300HCID 70563300, compound

Product 1

HCID 70563951HCID 70563951, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A sample of 4-chloro-α-methoxy-5-nitro-o-toluamide (0.8 g) is added to phosphorus oxychloride (10 ml) and the slurry gradually heated to reflux. After about 10 minutes at reflux, all the solid has dissolved giving a clear yellow solution. The solution is concentrated in vacuo and the crude residue is portioned between ether and water. The ether layer is separated and dried. Removal of the drying agent and concentration of the filtrate in vacuo leaves a crude solid (0.7 g.) with mp 57°-59°.

Workup

  1. temperaturethe slurry gradually heated to reflux
  2. temperatureAfter about 10 minutes at reflux
  3. dissolutionall the solid has dissolved
  4. customgiving a clear yellow solution
  5. concentrationThe solution is concentrated in vacuo
  6. customThe ether layer is separated
  7. customdried
  8. customRemoval of the drying agent and concentration of the filtrate in vacuo
  9. customleaves a crude solid (0.7 g.) with mp 57°-59°

Sources & evidence

ORD record
ord-126a01c6f0b3494b90e6e74c054d1fa2
Source dataset
uspto-grants-1981_10
Patent number
US04297127

Reaction notes

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