Pyridine → HCID 15580737, compound

HRID 543800Notes

Reaction equation

HRID 543800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][C:11]([NH:14][C:15](=[O:20])[C:16](F)(F)F)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[Cl:27][C:28]1[CH:36]=[CH:35]C(C(Cl)=O)=[CH:30][CH:29]=1>O>[Cl:27][C:28]1[CH:36]=[CH:35][C:16]([C:15]([NH:14][C:11]2[CH2:12][CH2:13][N:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[N:10]=2)=[O:20])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 15580707HCID 15580707, compound

Product 1

HCID 15580737HCID 15580737, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2.30 g. of 3-amino-1-(3,4-dichlorophenyl)-2-pyrazoline (prepared as described in Example 1) in 20 ml. of dry pyridine is cooled in an ice bath, then 2.10 g. of p-chlorobenzoyl chloride is added. The reaction mixture is allowed to stand at room temperature for 16 hours then is poured into water to separate a solid. The solid is collected by filtration and dissolved in dichloromethane. This solution is passed through a short column of a hydrous magnesium silicate. The effluent is refluxed and hexane is added until turbidity results. The solution is cooled and filtered to collect a product. The product is recrystallized from the same solvent pair to give 1.8 g. of the desired product as yellow needles, m.p. 177°-178° C.

Workup

  1. additionA stirred mixture of 2.30 g
  2. customto separate a solid
  3. filtrationThe solid is collected by filtration
  4. dissolutiondissolved in dichloromethane
  5. temperatureThe effluent is refluxed
  6. additionhexane is added until turbidity
  7. customresults
  8. temperatureThe solution is cooled
  9. filtrationfiltered
  10. customto collect a product
  11. customThe product is recrystallized from the same solvent pair
  12. customto give 1.8 g

Sources & evidence

ORD record
ord-3c48002d78b348fabd5d16231301c38f
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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