Iodoethane → HCID 15079057, compound

HRID 1111135Notes

Reaction equation

HRID 1111135 reaction equation
[Br:1][C:2]1[C:3](=[O:24])[NH:4][N:5]=[C:6]([NH2:23])[C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=1.Br[C:26]1C(=O)NN=C([N+]([O-])=O)[C:31]=1NCC1C=CC(OC)=C(OCCCC)C=1.C(I)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.CO.C(C(C)=O)C>[CH2:26]([N:4]1[C:3](=[O:24])[C:2]([Br:1])=[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=2)[C:6]([NH2:23])=[N:5]1)[CH3:31]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 15079054HCID 15079054, compoundHCID 15079055HCID 15079055, compound

Product 1

HCID 15079057HCID 15079057, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture comprising 280 mg of 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-amino-3(2H)pyridazinone (Compound No. 30) prepared according to the process of Example 3 from 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone (Compound No. 29) as the starting material, 0.29 ml of ethyl iodide, 487 mg of anhydrous potassium carbonate and 15 ml of methyl ethyl ketone, was refluxed under stirring for 2 hours. The solvent was distilled off under reduced pressure, and water was added to the residue thereby obtained. The mixture was extracted with chloroform. The extract was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. Then, the solvent was distilled off, the residue thereby obtained was subjected to silica gel thin layer chromatography by using a solvent mixture of chloroform:methanol (9:1 v/v) as the developer, the oily substance thereby obtained was crystallized from a solvent mixture of diethyl ether-n-hexane, to obtain 180 mg of the above identified compound having a melting point of from 108° to 110.5° C. as light yellow crystals.

Workup

  1. custom30) prepared
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customthereby obtained
  5. extractionThe mixture was extracted with chloroform
  6. washThe extract was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customthe residue thereby obtained
  10. customthe oily substance thereby obtained
  11. customwas crystallized from a solvent mixture of diethyl ether-n-hexane
  12. customto obtain 180 mg of the
  13. customof from 108° to 110.5° C.

Sources & evidence

ORD record
ord-9634190f2c194c6ca9ef27ba07440706
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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