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

HRID 1870764Notes

Reaction equation

HRID 1870764 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

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

Workup

  1. customThe mixture was evaporated, in vacuo, to dryness
  2. custompurified by MPLC

Sources & evidence

ORD record
ord-60ea28f0b7c94ab2aeda92774b31d8ab
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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