Iodoethane → N-Ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

HRID 1906822Notes

Reaction equation

HRID 1906822 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[N:8][C:7]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.[CH2:20](I)[CH3:21]>O1CCCC1>[CH2:20]([N:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:7]2[N:8]=[N:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[CH:11]=1)[C:17](=[O:19])[CH3:18])[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 15595701N-[3-(6-Chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 14280297N-Ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.0 g of sodium hydride (50% dispersion in oil) in 400 ml of anhydrous tetrahydrofuran was added 18.0 g of N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide. The solution was stirred for 0.5 hrs, then 6.4 ml ethyl iodide was added. After stirring for 18 hours, the reaction mixture was treated as described in Example 63 to give 19.8 g of colorless crystals, mp 116°-119° C. Recrystalization from acetone-hexane gave colorless crystals, mp 120°-121° C.

Workup

  1. stirringAfter stirring for 18 hours
  2. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-0791960c57d64b0282f09d392ad79f32
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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