2,3-Dichloropropene → Butyl 6-[N-(5-bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate

HRID 1870761Notes

Reaction equation

HRID 1870761 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]([CH2:35]Cl)=[CH2:34]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:35][C:33]([Cl:32])=[CH2:34])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 22622486butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylate

Product 1

HCID 18693232Butyl 6-[N-(5-bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 11) (0.28 g, 0.69 mmol) in DMF (4 ml) was treated with potassium carbonate (2.05 mmol) followed by 2,3-dichloroprop-1-ene (168 mg, 140 μl, 1.4 mmol) and the reaction stirred at ambient temperature over the weekend. The reaction mixture was evaporated to dryness, preabsorbed onto silica (1.5 g) and purified by MPLC to give the title compound as a colourless gum (0.24 g, 72%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompreabsorbed onto silica (1.5 g)
  3. custompurified by MPLC

Sources & evidence

ORD record
ord-d61f9462000a4fe5a1f65db2ec98b2be
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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