Water → 6-(5-chloropyridin-2-yl)-2-[4-(pentyloxy)but-2-ynyl]pyridazin-3(2H)-one

HRID 1968455Notes

Reaction equation

HRID 1968455 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:26][C:27]#[C:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=O)=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:26][C:27]#[C:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57907654HCID 57907654, compoundHCID 57907662HCID 57907662, compound

Product 1

HCID 444650956-(5-chloropyridin-2-yl)-2-[4-(pentyloxy)but-2-ynyl]pyridazin-3(2H)-oneYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 100 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 2.13 grams (g) of 6-(5-chloropyridin-2-yl)pyridazin-3(2H)-one (10.3 mmol), 2.20 g of potassium carbonate (16 mmol), and 50 mL of dry DMF. The reaction mixture was stirred for about 30 minutes at ambient temperature followed by the dropwise addition of 2.54 g of 4-(pentyloxy)but-2-ynyl methanesulfonate (10.8 mmol) in about 5 mL of dry DMF. The reaction was stirred overnight at ambient temperature, and checked by TLC and GC the next morning. No starting material remained, and one new product was formed. The reaction was poured into about 100 mL of water, and extracted with 3×50 mL of ethyl ether. The combined ether extract was washed with 100 mL of water, 100 mL of saturated aqueous sodium chloride solution, dried, and stripped to the crude product which was purified by silica gel column chromatography. The pure fractions were combined and concentrated under vacuum on a rotary evaporator to afford 1.3 g of a white solid. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 0.90 (m 3H); 1.30 (m, 4H); 1.55 (m, 2H); 3.45 (t, 2H); 4.15 (s, 2H); 5.05 (s, 2H); 7.05 (d, 1H); 7.75 (d, 1H); 8.15 (d, 1H); 8.30 (d, 1H); 8.55 (s, 1H).

Workup

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. customone new product was formed
  3. extractionextracted with 3×50 mL of ethyl ether
  4. extractionThe combined ether extract
  5. washwas washed with 100 mL of water, 100 mL of saturated aqueous sodium chloride solution
  6. customdried
  7. customwas purified by silica gel column chromatography
  8. concentrationconcentrated under vacuum on a rotary evaporator

Sources & evidence

ORD record
ord-1229c738bd02403882a3f70d92b559cd
Source dataset
uspto-grants-2013_04
Patent number
US08426412B2

Reaction notes

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