Water → 4,5-dichloro-2-methoxymethyl-2H-pyridazin-3-one

HRID 221854

Reaction equation

HRID 221854 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][NH:5][C:6](=[O:9])[C:7]=1[Cl:8].C(N(CC)C(C)C)(C)C.[CH3:19][O:20][CH2:21]Br.O>C(Cl)Cl>[Cl:8][C:7]1[C:6](=[O:9])[N:5]([CH2:19][O:20][CH3:21])[N:4]=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 732474,5-Dichloro-3-hydroxypyridazineHCID 81531DiisopropylethylamineHCID 83093Bromomethyl methyl ether

Product 1

HCID 123518344,5-dichloro-2-methoxymethyl-2H-pyridazin-3-oneYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4,5-dichloropyridazin-6-one (5.00 g, 30.3 mmol) and N,N-diisopropylethylamine (7.92 mL, 45.5 mmol) in methylenechloride (50 mL) was added slowly, bromomethyl methyl ether (4.79 mL, 60.6 mmol) at room temperature (water-bath). The reaction was stirred for 22 h and was then concentrated. Purification by column chromatography (1% MeOH in CH2Cl2) gave 4.74 g (74.8%) of 4,5-dichloro-2-methoxymethyl-2H-pyridazin-3-one.

Workup

  1. customat room temperature
  2. concentrationwas then concentrated
  3. customPurification by column chromatography (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ae0fd16c91574504896206a7ea4213f6
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Linked notes

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