Iodine → 1,3-Diethyl-4-iodo-5-methylpyrazole

HRID 1245586Notes

Reaction equation

HRID 1245586 reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH3:10])=[N:4]1)[CH3:2].CCCCCCCCCCCCCCCC(OCC(O)[C@H]1OC[C@H](O)[C@H]1O)=O.[I:39]I>[OH-].[Na+]>[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([I:39])[C:5]([CH2:9][CH3:10])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 807Iodine2×HCID 219127841,3-Diethyl-5-methylpyrazoleHCID 70687305(5xi)-1,4-Anhydro-6-O-hexadecanoyl-D-xylo-hexitol2×

Product 1

HCID 219127481,3-Diethyl-4-iodo-5-methylpyrazole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 13.2 g (95.7 mmol) of 1,3-diethyl-4-5-methylpyrazole (from Step C) and 1.50 g (3.7 mmol) of sorbitan monopalmitate in 200 mL of 2.5 N NaOH was treated with 44 g (0.17 mol) of iodine. Additional portions of sorbitan monopalmitate and iodine were added after 30 min and 60 min. The mixture was partitioned between 1 L of ether and 500 mL of water and the layers were separated. The organic layer was washed with 500 mL of 5% Na2S2O3, dried over MgSO4 and concentrated. Chromatography on a Biotage 75L using 9:1 heptane/EtOAc as the eluant afforded the title compound. 1H-NMR (400 MHz) δ 1.22 (t, J=7.6, 3H), 1.36 (t, J=7.2, 3H), 2.27 (s, 3H), 2.58 (q, J=7.6, 2H), 4.10 (q, J=7.2, 2H).

Workup

  1. customThe mixture was partitioned between 1 L of ether and 500 mL of water
  2. customthe layers were separated
  3. washThe organic layer was washed with 500 mL of 5% Na2S2O3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d6d5550671174c7487cdc141a816161f
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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