Sodium Methoxide → HCID 178489618, compound

HRID 433889

Reaction equation

HRID 433889 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH:6]([C:11]([O:13]C)=O)[C:7]([O:9]C)=O.C[O-].[Na+].Cl.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[NH:31])[NH2:30])[N:24]=1>CO>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[C:7]([OH:9])=[N:30][C:29]([C:25]2[N:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[N:31][C:11]=1[OH:13]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonateHCID 18756080Pyridazine-3-carboximidamide hydrochloride

Product 1

HCID 178489618HCID 178489618, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Dimethyl 2-(2-methoxyphenoxy)malonate (3.05 g, 12.6 mmol) (Ref. Canadian Patent Application No. CA2071193A, 1992) in methanol (15 ml) was added over 5 minutes to a stirred, 25% w/v solution of sodium methoxide in methanol (8.58 ml, 37.8 mmol of sodium methoxide) at room temperature. The resulting mixture was stirred for 10 minutes and then a solution of 3-pyridazinecarboximidamide hydrochloride (2.0 g, 12.6 mmol) in methanol (15 ml) was added dropwise over 5 minutes and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and then diluted with water (100 ml). The aqueous solution was acidified to pH 4 with sulfuric acid (20%), resulting in the formation of the title compound as a purple solid, which was isolated by filtration (1.4 g).

Workup

  1. customat room temperature
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additiondiluted with water (100 ml)

Sources & evidence

ORD record
ord-5ae723d3be3a4c6f8eaf110aa2f6e70d
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Linked notes

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