N-Iodosuccinimide → 1-cyclopropyl-4-iodo-1H-pyrazol-5-amine

HRID 1051684Notes

Reaction equation

HRID 1051684 reaction equation
[CH:1]1([N:4]2[C:8]([NH2:9])=[CH:7][CH:6]=[N:5]2)[CH2:3][CH2:2]1.[I:10]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([N:4]2[C:8]([NH2:9])=[C:7]([I:10])[CH:6]=[N:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 23665763Sodium BisulfiteHCID 833829061-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 1180757251-cyclopropyl-4-iodo-1H-pyrazol-5-amineYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100-mL round-bottom flask was charged with 1-cyclopropyl-1H-pyrazol-5-amine (0.410 g, 3.33 mmol) and N,N-dimethylformamide (10 mL). N-Iodosuccinimide (0.820 g, 3.64 mmol) was added, and the resulting solution stirred for 18 h at room temperature. The reaction mixture was poured into saturated aqueous sodium bisulfite solution (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1:1, ethyl acetate/petroleum ether) to afford 1-cyclopropyl-4-iodo-1H-pyrazol-5-amine (0.440 g, 48%) as light yellow oil. MS (ESI, pos. ion) m/z 250 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified via column chromatography on silica gel (eluting with 1:1, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7911927df6c34b0390c5e10d27bd124c
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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