Phosphorus oxychloride → HCID 178526742, compound

HRID 1953461Notes

Reaction equation

HRID 1953461 reaction equation
P(Cl)(Cl)([Cl:3])=O.[OH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11](O)[CH:10]=[CH:9][N:8]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:3][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([OH:6])[C:12]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526878HCID 178526878, compound

Product 1

HCID 178526742HCID 178526742, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Phosphorous oxychloride (63.4 mL, 0.68 mol) was added dropwise to a stirred mixture of 2,4-dihydroxy-3-nitropyridine (28.92 g, 0.17 mol) and benzyl triethylammonium chloride (155 g, 0.68 mol) in acetonitrile (560 mL). The reaction mixture was warmed to 60° C. for 1 h then was heated to reflux for 1 h. The reaction was cooled and the volatiles were evaporated in vacuo. An ice/water slurry (500 mL) was added to the residual oil and the mixture was stirred for 3 h at 0° C. The solids were collected by filtration, washing with water and hexanes to give the title compound as a solid;

Workup

  1. temperaturethen was heated
  2. temperatureto reflux for 1 h
  3. temperatureThe reaction was cooled
  4. customthe volatiles were evaporated in vacuo
  5. additionAn ice/water slurry (500 mL) was added to the residual oil
  6. filtrationThe solids were collected by filtration
  7. washwashing with water and hexanes

Sources & evidence

ORD record
ord-186bd1d5985a44fca4939ae96d3c38f8
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

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