Phosphorus oxychloride → HCID 20373304, compound

HRID 1834403Notes

Reaction equation

HRID 1834403 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH:14]=[N:15]O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].O=P(Cl)(Cl)Cl>C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]#[N:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 73676740HCID 73676740, compound

Product 1

HCID 20373304HCID 20373304, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A stirred mixture of 5-(4-cyanophenyl)-2-furaldehyde oxime (16 g, 0.075 mole) and benzene (400 ml) was heated to reflux and a solution of POCl3 (4 ml) in benzene (20 ml) was added dropwise over 15 minutes. The mixture was refluxed for 11/2 hours and filtered while hot. The filtrate was washed with 5% NaHCO3 (500 ml), H2O (500 ml), dried over MgSO4 and Darco and filtered. The filtrate was stripped of solvent under reduced pressure to yield 10 g (69%) of 5-(4-cyanophenyl)-2-furonitrile.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 11/2 hours
  4. filtrationfiltered while hot
  5. washThe filtrate was washed with 5% NaHCO3 (500 ml), H2O (500 ml)
  6. dry with materialdried over MgSO4 and Darco
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b24bba1358e748278d17e6c7f325250b
Source dataset
uspto-grants-1978_01
Patent number
US04070380

Reaction notes

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