Bromine → Ethyl 2-bromo-2-(2-(6-chloropyridazin-3-yl)hydrazono)acetate

HRID 521575Notes

Reaction equation

HRID 521575 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[N:7][NH:8][C:9]1[N:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+].[Br:21]Br>CC(O)=O.O>[Br:21][C:6](=[N:7][NH:8][C:9]1[N:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 71367215Acetic acid, [(6-chloro-3-pyridazinyl)hydrazono]-, ethyl ester

Product 1

HCID 89287509Ethyl 2-bromo-2-(2-(6-chloropyridazin-3-yl)hydrazono)acetateYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of compound 1-ethoxycarbonylmethylene-2-(6-chloro-3-pyridazinyl) hydrazine (11.4 g, 0.05 mol) and sodium acetate (11 g, 0.05 mol) in 50 mL of HOAc, bromine (8 g, 0.05 mol) in HOAc was added dropwise during 20 min. Stirring was continued for 3 h, the mixture was diluted with water (1 L), the precipitated crystals were filtered off, washed with water to give product ethyl 2-bromo-2-(2-(6-chloropyridazin-3-yl)hydrazono)acetate as a yellow solid (10 g, 66%). 1H NMR (300 MHz, d6-DMSO): δ 9.33 (br, 1H), 7.69-7.66 (d, J=9.0 Hz, 1H), 7.50-7.47 (d, J=9.0 Hz, 1H), 4.44-4.37 (q, 2H), 1.43-1.39 (t, 3H).

Workup

  1. filtrationthe precipitated crystals were filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-8f4ffd5f292546c1835f133745cdaead
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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