Potassium Carbonate → HCID 58371919, compound

HRID 1020964Notes

Reaction equation

HRID 1020964 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[CH:5][CH:6]=1.[N:8]1[NH:9][C:10](=[O:14])[CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.C1(C)C=CC=CC=1>[Br:1][C:2]1[S:3][C:4]([N:9]2[C:10](=[O:14])[CH:11]=[CH:12][CH:13]=[N:8]2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 184532,5-DibromothiopheneHCID 681533(2H)-PyridazinoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 58371919HCID 58371919, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,5-dibromothiophene (1.5 g, 6.2 mmol), pyridazin-3(2H)-one (0.4 g, 4.1 mmol), copper(I) iodide (0.24 g, 1.2 mmol), potassium carbonate (1.7 g, 12.4 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.2 mL, 1.2 mmol) and toluene (15 mL) was degassed for 15 minutes and then heated in a sealed tube at 110° C. for 18 hours. Cooled to room temperature, filtered through celite and washed with EtOAc. The filterate was washed with water (100 mL×2). The organic layer was dried over Na2SO4, filtered and concentrated give the desired product 2BZ (0.9 g, 90%). The residue was purified on silica gel eluting with 80% EtOAc/hexane to give the desired product 2BZ (0.7 g, 67%).

Workup

  1. customwas degassed for 15 minutes
  2. temperatureCooled to room temperature
  3. filtrationfiltered through celite
  4. washwashed with EtOAc
  5. washThe filterate was washed with water (100 mL×2)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a45eb3675995476ea572d0018e4bbc2a
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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