Potassium Carbonate → HCID 86659378, compound

HRID 2043397

Reaction equation

HRID 2043397 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[N:9]=1)[CH:5]=[O:6].C1(C)C=CC(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:22]=[N:21][CH:20]=2)[CH:7]=[C:8]([Cl:10])[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 27610242,6-Dichloropyridine-4-carbaldehyde

Product 1

HCID 86659378HCID 86659378, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

528 mg of 2,6-dichloroisonicotinaldehyde (this compound was prepared by the method described in J. Chem. Soc., Chem. Commun., 1998, 1567-1568) was dissolved in 10 ml of methanol, and 586 mg of p-toluenesulfonyl methyl isocyanide and 415 mg of potassium carbonate ware added, and the mixture was stirred at 50° C. for 30 minutes. The reaction solution was concentrated, and then diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 630 mg of the objective compound as white powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-544006946f2649d186b590ddf0aa1e14
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Linked notes

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