Water → HCID 22730545, compound

HRID 2356063Notes

Reaction equation

HRID 2356063 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 770224-Iodopyrazole

Product 1

HCID 22730545HCID 22730545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-iodopyrazole (11.25 g, 6.44 mmol) in DMF (20 mL) at room temperature was treated with 60% NaH (271 mg, 6.77 mmol), stirred for 10 minutes, treated with 1-bromooctane (1.22 mL, 7.08 mmol), stirred for 30 minutes, poured into water, and extracted three times with ether/hexanes. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 307 (M+H)+.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted three times with ether/hexanes
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b2fb2611f1a4c2c9cf681cda8b5560f
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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