Iodine → 1-Pyrazolyl iodopropargyl ether

HRID 652698Notes

Reaction equation

HRID 652698 reaction equation
[I:1]I.[CH2:3]([O:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1)[C:4]#[CH:5].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[I:1][CH:3]([O:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1)[C:4]#[CH:5]

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 201962031-Pyrazolyl propargyl ether

Product 1

HCID 201961981-Pyrazolyl iodopropargyl etherYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

41.6 g of iodine are added, a little at a time, to 20 g of 1-pyrazolyl propargyl ether and 20 g of sodium carbonate in 400 g of acetonitrile at 40° C., while stirring. Stirring is continued for 8 hours at 40° C., after which undissolved material is filtered off under suction, and the filtrate is evaporated down in a rotary evaporator at 30° C. and under 20 mbar. The residue is dissolved in 200 g of dichloromethane, the solution is extracted twice with 200 g of 10% strength aqueous sodium thiosulfate solution, and the organic phase is dried with magnesium sulfate and evaporated down. 40 g (99% of theory) of 1-pyrazolyl iodopropargyl ether are obtained as an oil (H1 --NMR, in ppm: 5.1, s, 2H; 6.2, m, 1H; 7.4, m, 2H).

Workup

  1. filtrationafter which undissolved material is filtered off under suction
  2. customthe filtrate is evaporated down in a rotary evaporator at 30° C. and under 20 mbar
  3. dissolutionThe residue is dissolved in 200 g of dichloromethane
  4. extractionthe solution is extracted twice with 200 g of 10% strength aqueous sodium thiosulfate solution
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. customevaporated down

Sources & evidence

ORD record
ord-ec7c0d6077134811a13af3487d0043fc
Source dataset
uspto-grants-1987_06
Patent number
US04673429

Reaction notes

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