Triethylamine → Methyl-phenyl-carbamic Acid 4,5-dichloro-pyridazin-3-yl Ester

HRID 1831247Notes

Reaction equation

HRID 1831247 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[N:4][C:3]=1[OH:9].[CH3:10][N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12](Cl)=[O:13].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[N:4][C:3]=1[O:9][C:12](=[O:13])[N:11]([CH3:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178518919HCID 178518919, compound

Product 1

HCID 69517447Methyl-phenyl-carbamic Acid 4,5-dichloro-pyridazin-3-yl EsterYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-dichloro-3-hydroxypyridazine (0.49 g, 3.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.51 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in tetrahydrofuran (15 ml) was stirred at room temperature for 3 days. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80)) yielding the title compound (0.12 g, 14% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80))

Sources & evidence

ORD record
ord-5d6efe77510a4705a1be16a9910cd226
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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