ChemicalBook CAS DataBase List 4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE

4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE synthesis

5synthesis methods

Product Name:4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE
CAS Number:51660-65-2
Molecular formula:C6H9IN2
Molecular Weight:236.05

2033-45-6 Synthesis

2033-45-6
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$6.00/1g

74-88-4
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$15.00/10g

51660-65-2
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$39.00/250mg

Yield:51660-65-2 97%

Reaction Conditions:

Stage #1: 4-iodo-3,5-dimethyl-1H-pyrazolewith sodium hydride in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: methyl iodide in tetrahydrofuran; for 12 h;

Steps:

4-Iodo-1,3,5-trimethyl-1H-pyrazole 6b

Under an atmosphere of nitrogen a solution of 4-iodo-3,5-dimethyl-1H-pyrazole (8.95 g; 40.0 mmol) inanhyd. THF was added dropwise to a freshly prepared suspension of sodium hydride (1.06 g; 44.0 mmol).The reaction mixture was stirred for 3 h and then 5.0 mL of methyl iodide (11.94 g; 88.0 mmol) were added dropwise. The mixture was stirred for additional 12 h and then quenched by adding approximately50 mL of water. The crude product was extracted with Et2O and dried over sodium sulfate. Afterevaporation of the solvent the product was obtained as a yellowish solid. Yield: 9.18 g (97%)

References:

Ahlburg, Nils Lennart;Doppleb, Olivia;Hillrichs, Kai;Namyslo, Jan C.;Hübner, Eike G.;Schmidt, Andreas [Heterocycles,2018,vol. 96,# 7,p. 1203 - 1215]