Water → HCID 22247813, compound

HRID 889850Notes

Reaction equation

HRID 889850 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CC(C)([O-])C.[K+].Br[CH2:14][CH2:15][CH2:16][Cl:17].O>CN(C=O)C>[Cl:17][CH2:16][CH2:15][CH2:14][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 770224-IodopyrazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 22247813HCID 22247813, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (10.31 mmol) 4-iodopyrazole were dissolved in 20 ml DMF and 1.22 g (10.8 mmol) potassium t-butoxide was added. The mixture was stirred for 1 hour at room temperature and 1.06 ml (10.83 mmol) 1-bromo-3-chloropropane were added. A white precipitate appeared rapidly. After 30 minutes 50 ml water was added and the reaction mixture was extracted twice with 100 ml hexane. The combined organic layers were dried over MgSO4 and the solvent was removed to give 2.65 g of the desired product as a colourless oil. MS (ISP): 270.1 (MH+). 1H-NMR (CDCl3): 2.31 (quint, 2H), 3.47 (t, 2H), 4.32 (t, 2H), 7.48 (s, 1H), 7.53 (s, 1H).

Workup

  1. extractionthe reaction mixture was extracted twice with 100 ml hexane
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-9f4751896ca14872b6f389820593e543
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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