Isopropyl iodide → HCID 67261906, compound

HRID 2359095Notes

Reaction equation

HRID 2359095 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([I:12])=[C:10]([CH3:13])[NH:9][N:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH:17]([CH3:19])[CH3:18].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([I:12])=[C:10]([CH3:13])[N:9]([CH:17]([CH3:19])[CH3:18])[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67260755HCID 67260755, compound

Product 1

HCID 67261906HCID 67261906, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-(5-Chloro-2-thienyl)-4-iodo-5-methyl-1H-pyrazole (31.9 mmol) was dissolved in 30 mL dry N,N-dimethylformamide and cooled to 0° C. under nitrogen atmosphere. Sodium hydride (33.5 mmol, 60% dispersion in mineral oil) was added in portions at 0° C. After stirring for 30 min, 2-iodopropane (38.5 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was poured into saturated aqueous ammonium chloride solution and extracted with diethyl ether, dried over MgSO4, filtered and evaporated. The crude product was purified by chromatography on silica gel (cyclohexane:dichloromethane 90:10) to afford 7.5 g 3-(5-chloro-2-thienyl)-4-iodo-1-isopropyl-5-methyl-1H-pyrazole (67% yield)

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred overnight
  3. extractionextracted with diethyl ether
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by chromatography on silica gel (cyclohexane:dichloromethane 90:10)

Sources & evidence

ORD record
ord-b55883684b81446fad7505b2520803cf
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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