Potassium Iodide → HCID 67004094, compound

HRID 1811364Notes

Reaction equation

HRID 1811364 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1.[I-].[K+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C>[CH2:15]([N:1]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 89191-BromododecaneHCID 152505475-amino-2H-1,3-benzodiazol-2-one

Product 1

HCID 67004094HCID 67004094, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Aminobenzimidazolone (0.1348 g, 0.904 mmol), potassium iodide (0.1513 g, 0.911 mmol), and dry DMF (20 mL) are mixed in a 100 mL round bottom flask under an inert atmosphere. The reaction is heated to 60° C. and 1-bromododecane (0.45 mL, 1.88 mmol) is added. After 3 days at 60° C., the reaction is cooled to room temperature to give a brown suspension. The solid is filtered, washed with deionized water, and dried in vacuo to give 5-(didodecylamino)-2-benzimidazolone as a white solid (0.334 g). The product is identified by 1H and 13C NMR spectroscopy and ESI-MS and is of satisfactory purity.

Workup

  1. temperaturethe reaction is cooled to room temperature
  2. customto give a brown suspension
  3. filtrationThe solid is filtered
  4. washwashed with deionized water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ce5c4a37e706477381b61246645e72f2
Source dataset
uspto-grants-2013_01
Patent number
US08362270B2

Reaction notes

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