Triethylamine → 2-Bromo-N-(6-methyl-pyridazin-3-yl)-acetamide

HRID 2192376Notes

Reaction equation

HRID 2192376 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][C:7]1[N:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]([NH:6][C:7]1[N:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 877126-Methylpyridazin-3-amine

Product 1

HCID 673108012-Bromo-N-(6-methyl-pyridazin-3-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromoacetyl bromide (0.22 mL) in dry CHCl3 (4 mL) was added slowly to a suspension of 3-amino-6-methylpyridazine (0.24 g) and triethylamine (0.47 mL) in dry CHCl3 (45 mL) at room temperature. The brown mixture was allowed to stir for 3.5 hr, then quenched with H2O (1.5 mL) and stirred for 20 mins before concentrating under reduced pressure to a brown solid. The crude product was purified by silica gel chromatography eluting with 1-2% MeOH/dichloromethane. The relevant fractions were combined and evaporated to give the title compound (0.20 g) as a pinkish/beige solid.

Workup

  1. customquenched with H2O (1.5 mL)
  2. stirringstirred for 20 mins
  3. concentrationbefore concentrating under reduced pressure to a brown solid
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with 1-2% MeOH/dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-f936bb35d18b4f92b12d235e0b7d0eff
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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