1,6-Diiodohexane → HCID 73979842, compound

HRID 1813953Notes

Reaction equation

HRID 1813953 reaction equation
[H-].[Na+].[Cl:3][C:4]1[S:5][C:6]([CH2:9][N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[N:15][N+:16]([O-:18])=[O:17])=[CH:7][N:8]=1.I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]I>CN(C=O)C>[Cl:3][C:4]1[S:5][C:6]([CH2:9][N:10]2[CH2:14][CH2:13][N:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:12]3[CH2:13][CH2:14][N:10]([CH2:9][C:6]4[S:5][C:4]([Cl:3])=[N:8][CH:7]=4)[C:11]3=[N:15][N+:16]([O-:18])=[O:17])[C:11]2=[N:15][N+:16]([O-:18])=[O:17])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 123731,6-DiiodohexaneHCID 24758Sodium hydrideHCID 136355710HCID 136355710, compound

Product 1

HCID 73979842HCID 73979842, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (60%, 0.48 g, 12 mmol) in 20 ml of DMF was prepared. 1-(2-Chloro-5-thiazolylmethyl)-2-nitroiminoimidazolidine (2.61 g, 10 mmol) was added to this suspension. The resulting mixture was then stirred for 1 hour at room temperature. 1,6-Diiodohexane (1.64 g, 5 mmol) was added dropwise to this reaction mixture over the course of 30 minutes while cooling the reaction mixture with ice. Following completion of dropping, the mixture was stirred for 4 hours at room temperature. The DMF was distilled off from the reaction mixture under reduced pressure. The residue was then shaken with a mixture of water and chloroform. After separating the chloroform layer and drying, the solvent was distilled off under reduced pressure. The semi-solid residue was subjected to silica gel column chromatography with a mixture (15:1 (v/v)) of ethyl acetate and ethanol as the eluate. The crude product was recrystallized from methanol. The yield of crystalline product was 0.22 g (70%), and the melting point was 204 to 206° C. The results of elementary analysis and NMR analysis are shown below.

Workup

  1. customwas prepared
  2. temperaturewhile cooling the reaction mixture with ice
  3. stirringthe mixture was stirred for 4 hours at room temperature
  4. distillationThe DMF was distilled off from the reaction mixture under reduced pressure
  5. stirringThe residue was then shaken with a mixture of water and chloroform
  6. customAfter separating the chloroform layer
  7. customdrying
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was recrystallized from methanol
  10. customThe results of elementary analysis and NMR analysis

Sources & evidence

ORD record
ord-14dede25055d4649bf1859f5ef30559f
Source dataset
uspto-grants-2005_04
Patent number
US06875778B2

Reaction notes

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