Sodium Iodide → HCID 21872631, compound

HRID 723295Notes

Reaction equation

HRID 723295 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[C:10]([O:13][CH2:14][CH2:15][CH2:16]Br)(=[O:12])[CH3:11].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O>[C:10]([O:13][CH2:14][CH2:15][CH2:16][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 5798BenzimidazoleHCID 8471TriethylamineHCID 122357751-Propanol, 3-bromo-, 1-acetate

Product 1

HCID 21872631HCID 21872631, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a nitrogen atmosphere, a mixture of 118 g of benzimidazole, 181 g of 3-bromopropyl acetate, 111 g of triethylamine, 2 g of sodium iodide, and 500 g of N,N-dimethylformamide was heated and stirred at 80° C. for 16 hours. The reaction mixture was subjected to conventional aqueous work-up and then purified by column chromatography, obtaining 3-(1H-benzimidazol-1-yl)propyl acetate (yield 70%).

Workup

  1. temperaturewas heated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-5ea63fb43db24ffca6547c8221329ddd
Source dataset
uspto-grants-2006_11
Patent number
US07141352B2

Reaction notes

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