Hydrochloric Acid → HCID 13853902, compound

HRID 2372352Notes

Reaction equation

HRID 2372352 reaction equation
[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH:9]([CH3:11])[CH3:10])[N:5]=[CH:6][C:7]=1[NH2:8].[H-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CN(C)C=O.C1C=CC=CC=1>[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH:9]([CH3:10])[CH3:11])[N:5]=[CH:6][C:7]=1[NH:8][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 19903153HCID 19903153, compound

Product 1

HCID 13853902HCID 13853902, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

In 6 ml of dry dimethylformamide, 1.875 g of 4-chloro-5-amino-2-i-propyl-3(2H)pyridazinone was dissolved. 0.48 g of sodium hydride (50% mineral oil suspension) was added thereto at a temperature of from 5° to 10° C., and the mixture was stirred for about 30 minutes. Then, 1.4 g of benzyl chloride was dropwise added thereto at the same temperature. After the dropwise addition, the mixture was stirred at room temperature for 2 hours. To the reaction solution, 50 ml of benzene and 30 ml of a 10% hydrochloric acid aqueous solution were added, and the mixture was vigorously shaken. The organic layer was washed with water, and dried, and then the solvent was distilled off. The crude crystals thereby obtained were recrystallized from ethyl ether to obtain 2.3 g of the above identified compound having a melting point of from 131° to 132° C.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was vigorously shaken
  4. washThe organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe crude crystals thereby obtained
  8. customwere recrystallized from ethyl ether
  9. customto obtain 2.3 g of the
  10. customof from 131° to 132° C.

Sources & evidence

ORD record
ord-648272f5a74e419193bdf6de916e62af
Source dataset
uspto-grants-1992_03
Patent number
US05098900

Reaction notes

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