Water → N-Methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

HRID 1906821Notes

Reaction equation

HRID 1906821 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.[CH3:20]I.O>O1CCCC1>[CH3:20][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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15595701N-[3-(6-Chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595702N-Methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.0 g of sodium hydride (50% dispersion in oil) in 300 ml of anhydrous tetrahydrofuran under argon was added 14.0 g of N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide. The solution was stirred for 0.5 hours, then 3.9 ml of methyl iodide was added. After stirring for 2 hours, the solution was poured onto 400 ml of water and extracted with 100 ml portions of dichloromethane. The combined extracts were dried, concentrated in vacuo and chromatographed on hydrated magnesium silicate with dichloromethane-methanol (98:2) as eluant. The fractions containing the desired product were combined, concentrated in vacuo and recrystalized from acetone-hexane to give 14.1 g of cream crystals, mp 109°-112° C.

Workup

  1. stirringAfter stirring for 2 hours
  2. extractionextracted with 100 ml portions of dichloromethane
  3. customThe combined extracts were dried
  4. concentrationconcentrated in vacuo
  5. customchromatographed on hydrated magnesium silicate with dichloromethane-methanol (98:2) as eluant
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated in vacuo
  8. customrecrystalized from acetone-hexane

Sources & evidence

ORD record
ord-24ae0241f97c4992869a8e058cfcc700
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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