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

HRID 329643Notes

Reaction equation

HRID 329643 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 (or 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. Recrystallization from acetone-hexane gave colorless crystals, mp 120°-121° C.

Workup

  1. stirringAfter stirring for 18 hours the reaction mixture
  2. additionwas treated

Sources & evidence

ORD record
ord-8070ffa3c41044a2b576d02605da712b
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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