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

HRID 1906799Notes

Reaction equation

HRID 1906799 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].CN(C)C=O.[CH2:25](I)[CH3:26]>O>[CH2:25]([N:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:9]=1)[C:15](=[O:17])[CH3:16])[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 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 962WaterSolvent

Procedure

A mixture of 4.0 g of N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide, 0.85 g of sodium hydride (50% in oil) and 300 ml of dry dimethylformamide, under argon, was stirred for 1 hour then 1.42 ml of ethyl iodide was added. After stirring for 2.5 hours, 0.5 equivalent of sodium hydride and 1.1 equivalent of ethyl iodide were added. This mixture was stirred overnight, poured into 1 liter of water and extracted with five 100 ml portions of dichloromethane. The extracts were combined, dried and evaporated in vacuo, giving 3.6 g of the desired compound as tan crystals, mp 105°-110° C.

Workup

  1. stirringAfter stirring for 2.5 hours
  2. stirringThis mixture was stirred overnight
  3. extractionextracted with five 100 ml portions of dichloromethane
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-407d2b48bc664405b031b169a20b2ee5
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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