Phosphorus oxychloride → 3-(6-Chloro-4-methyl-3-pyridazinyl)benzonitrile

HRID 372718Notes

Reaction equation

HRID 372718 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]([CH3:16])=[CH:11][C:12](=O)[NH:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].CC1C(C2C=CC=C(C#N)C=2)=NNC(=O)C1.[Cl:33]C1C=C(C2C(C)CC(=O)NN=2)C=CC=1.P(Cl)(Cl)(Cl)=O>>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][C:12]([Cl:33])=[CH:11][C:10]=2[CH3:16])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 12726871HCID 12726871, compoundHCID 12726872HCID 12726872, compoundHCID 20326533HCID 20326533, compound

Product 1

HCID 127268433-(6-Chloro-4-methyl-3-pyridazinyl)benzonitrile

Procedure

A 2.95 g. portion of 6-(m-cyanophenyl)-5-methyl-3(2H)-pyridazinone [prepared as described in Example 8 but employing 4,5-dihydro-5-methyl-6-(m-cyanophenyl)-3(2H)-pyridazinone (which in turn is prepared by employing 6-(m-chlorophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone in Example 44 of U.S. Pat. No. 3,824,271)] and 35 ml. of phosphorus oxychloride are heated on a steam bath for 5 hours. The mixture is concentrated free of excess phosphorus oxychloride and the concentrate is diluted with ice water. The resulting product, a tan solid, is recovered by filtration, washed with water and dried, m.p. 153°-155° C.

Workup

  1. customis prepared
  2. concentrationThe mixture is concentrated free of excess phosphorus oxychloride
  3. additionthe concentrate is diluted with ice water
  4. filtrationThe resulting product, a tan solid, is recovered by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-327fb777695240bba63f225dd07fa801
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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