Sodium Carbonate → Carbazic acid, 3-(6-(diallylamino)pyridazin-3-yl)-, ethyl ester
Reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][CH:10]=[CH2:11])=[CH:6][CH:7]=1.[C:15]([NH:20][NH2:21])([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:15]([NH:20][NH:21][C:2]1[N:3]=[N:4][C:5]([N:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][CH:10]=[CH2:11])=[CH:6][CH:7]=1)([O:17][CH2:18][CH3:19])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 4.18 g (0.02 moles) 3-chloro-6-diallylaminopyridazine and 4.16 g (0.04 moles) monocarbethoxyhydrazine is warmed up to 140° C and kept at this temperature for 1 hour. The mixture is taken up with cool water and sodium carbonate is added until neutral pH. It is then extracted with methylene chloride, the organic extracts collected together, dried over sodium sulphate and concentrated. The residual oil is purified by chromatography on silica gel column, eluting with a mixture of chloroform-methanol 9.5:0.5. The unitary fractions on thin layer chromatography with the same Rf are collected together; the solvent is eliminated by evaporation and a yellow oil formed by a 3-(2-carbethoxyhydrazino)-6-diallylaminopyridazine is obtained.
Workup
- additionis added until neutral pH
- extractionIt is then extracted with methylene chloride
- customthe organic extracts collected together
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customThe residual oil is purified by chromatography on silica gel column
- washeluting with a mixture of chloroform-methanol 9.5:0.5
- customThe unitary fractions on thin layer chromatography with the same Rf are collected together
- customthe solvent is eliminated by evaporation
Sources & evidence
- ORD record
- ord-7d97c9942d2a49cbb7384b76523db978
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04002753
Reaction notes
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