Sodium hydride → 4-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

HRID 1042559Notes

Reaction equation

HRID 1042559 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].[H][H].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 770224-IodopyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 574219364-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazoleYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-iodo-1H-pyrazole (1.50 g, 7.73 mmol) in dry DMF (15 mL) at 0° C. was added sodium hydride (9.28 mmol, 60% dispersion in mineral oil) and the reaction mixture was allowed to warm to room temperature. After the evolution of hydrogen had ceased, 4-methoxy-benzyl chloride (1.06 mL, 7.80 mmol) was added and the reaction was stirred for 2 h and then quenched with water (50 mL) and extracted with diethyl ether (100 mL). The organic layer was washed with water (3×30 mL) and brine, dried over magnesium sulphate and the solvent removed under vacuum. The crude residue was washed with small portions of hexane and dried in vacuo, providing the product as a white solid (2.26 g, 93% yield). 1H-NMR (CDCl3) δ 7.51 (s, 1H), 7.34 (s, 1H), 7.17 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 5.21 (s, 2H), 3.78 (s, 3H).

Workup

  1. customquenched with water (50 mL)
  2. extractionextracted with diethyl ether (100 mL)
  3. washThe organic layer was washed with water (3×30 mL) and brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under vacuum
  6. washThe crude residue was washed with small portions of hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-28433a8f402348b2bcc4c6a9de720fca
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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