N,N-Dimethylaniline → 3-Chloro-6-(3-methyl-5-chloro-1-pyrazolyl)-pyridazine

HRID 27894Notes

Reaction equation

HRID 27894 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[C:12](O)=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:17])=O.CN(C)C1C=CC=CC=1>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[C:12]([Cl:17])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178429261HCID 178429261, compound

Product 1

HCID 125628303-Chloro-6-(3-methyl-5-chloro-1-pyrazolyl)-pyridazine

Conditions

Temperature
0 °C

Procedure

To the mixture of 12.6 /0.04 moles/ of 3-chloro-6-(3-methyl-5-hydroxy-1-pyrazolyl)-pyridazine and 48 ml of phosphorus oxychloride, 7.28 g /0.04 moles/ of dimethyl aniline are dropped under stirring at 0° C. during half an hour, then the reaction mixture is stirred at room temperature for one hour and at boiling temperature for 2 hours. Excess of the phosphorus oxychloride is evaporated under reduced pressure, then the residue is poured into water and set aside overnight. The separated precipitate is filtered, washed with water and dried. Yield: 10.5 g (93%); m.p.: 123°-126° C.

Workup

  1. additionare dropped
  2. stirringthe reaction mixture is stirred at room temperature for one hour
  3. customfor 2 hours
  4. customExcess of the phosphorus oxychloride is evaporated under reduced pressure
  5. additionthe residue is poured into water
  6. filtrationThe separated precipitate is filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-eef4ce6b3b1249df9a4b9ff555de8d47
Source dataset
uspto-grants-1980_09
Patent number
US04224325

Reaction notes

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