Sodium Iodide → HCID 178447698, compound

HRID 2103951Notes

Reaction equation

HRID 2103951 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[Na+].[I-].[SH:9][C:10]1[N:14]=[CH:13][NH:12][N:11]=1>CO>[CH2:2]([S:9][C:10]1[N:14]=[CH:13][NH:12][N:11]=1)[CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 707041-Pentene, 5-bromo-HCID 178527894HCID 178527894, compound

Product 1

HCID 178447698HCID 178447698, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-bromopent-1-ene (10 mmol) and NaI were dissolved in 30 ml MeOH and stirred at room temperature for 12 h. 10 mmol 3-mercapto-1H-1,2,4-triazole (potassium salt) in 10 ml MeOH was added to above solution and further stirred for 24 hours. After the solvent MeOH was evaporated in vacuum, a mixture of hexane and ethyl acetate (1/1 in volume) 100 ml was added and stirred for 5 minutes. The precipitate was removed by filtration. The solvent in the filtrate was removed in vacuum. The residual was separated with a Si gel column (solvents: 1 ethyl acetate/1 hexane in volume). 1.2 g product was obtained as colorless oil. Yield: 71%. 1H NMR (CDCl3): 10.83 (1H, brs.), 8.17 (1H, s), 5.75 (1H, m), 4.99 (2H, m), 3.16 (2H, t), 2.19 (2H, m), 1.82 (2H, m).

Workup

  1. stirringfurther stirred for 24 hours
  2. customAfter the solvent MeOH was evaporated in vacuum
  3. additiona mixture of hexane and ethyl acetate (1/1 in volume) 100 ml
  4. additionwas added
  5. stirringstirred for 5 minutes
  6. customThe precipitate was removed by filtration
  7. customThe solvent in the filtrate was removed in vacuum
  8. customThe residual was separated with a Si gel column (solvents: 1 ethyl acetate/1 hexane in volume)

Sources & evidence

ORD record
ord-9b8c7fc6745344398f7d8481254325e2
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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