Sodium hydride → HCID 58790081, compound

HRID 418655Notes

Reaction equation

HRID 418655 reaction equation
[I:1][C:2]1[NH:3][C:4]([I:8])=[C:5]([I:7])[N:6]=1.[H-].[Na+].I[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.I>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[N:3]([CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:4]([I:8])=[C:5]([I:7])[N:6]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 24841Hydrogen iodideHCID 744592,4,5-TriiodoimidazoleHCID 23033725HCID 23033725, compound

Product 1

HCID 58790081HCID 58790081, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4,5-triiodo-1H-imidazole (165) (4.08 g, 9.1 mmol) in DMF (28 mL) at 0° C., was added NaH (1.46 g, 36.4 mmol) portionwise over 30 mins. Then 1-(2-iodoethyl)pyrrolidine×HI 164 (4.85 g, 13.65 mmol) was added at 0° C., and the reaction mixture was allowed to warm to room temperature over a period of 4 hrs. EtOAc (50 mL) was added and the mixture was washed with NaHCO3 aqueous solution. The organic phase was separated and extracted with citric acid solution (3%), the acidic aqueous extract was basified with 2N NaOH solution to pH˜10, the resultant solid was collected by filtration to give the title compound 166 (1.75 g, 35%) as a light brown solid. MS (m/z): 543.5 (M+H).

Workup

  1. washthe mixture was washed with NaHCO3 aqueous solution
  2. customThe organic phase was separated
  3. extractionextracted with citric acid solution (3%)
  4. extractionthe acidic aqueous extract
  5. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-72b7278cca124070a23c7d6e62b7f500
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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