2-Iodobutane → HCID 67260693, compound

HRID 2359071Notes

Reaction equation

HRID 2359071 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[CH:9][NH:8][N:7]=1.[H-].[Na+].I[CH:14]([CH2:16][CH3:17])[CH3:15].C(N1C=CC(C2SC=CC=2)=N1)(CC)C>CN(C)C=O.CC(OC)(C)C.O>[CH:14]([N:7]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:9]=[N:8]1)([CH2:16][CH3:17])[CH3:15]

Participants

8

Reactant 4

HCID 105592-IodobutaneHCID 24758Sodium hydrideHCID 67260913HCID 67260913, compoundHCID 178420845HCID 178420845, compound

Product 1

HCID 67260693HCID 67260693, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

3-(2-thienyl)-1H-pyrazole (23.2 mmol) was dissolved in 100 mL dry N,N-dimethylformamide and cooled to 0° C. under argon atmosphere. Sodium hydride (28.0 mmol, 60% dispersion in mineral oil) was added in portions at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 15 min. After cooling to 0° C. again, 2-iodobutane (35.0 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 14 h. Water and MTBE were added to the reaction mixture. The phases were separated and the aqueous phase was extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated. 650 mg of a mixture of 1-sec-butyl-3-(2-thienyl)-1H-pyrazole and 1-sec-butyl-5-(2-thienyl)-1H-pyrazole (82:18; 13% yield) were obtained.

Workup

  1. temperatureto warm to room temperature
  2. temperatureAfter cooling to 0° C. again
  3. stirringThe reaction mixture was stirred at room temperature for 14 h
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with MTBE
  6. washThe combined organic extracts were successively washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-527583c034a24b9abb22215b5d7d1f1e
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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