Sodium Iodide → 1,3-dihydro-1-(3-iodopropyl)-3-methyl-2H-benzimidazol-2-one

HRID 1751003Notes

Reaction equation

HRID 1751003 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH3:16])[C:8]1=[O:17]>CC(C)=O>[I:1][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH3:16])[C:8]1=[O:17]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 133608921-(3-chloropropyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 219899771,3-dihydro-1-(3-iodopropyl)-3-methyl-2H-benzimidazol-2-oneYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (3.43 g, 22.89 mmol, 2 equiv) was added to a solution of 1-(3-chloropropyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (2.57 g, 11.44 mmol, 1 equiv) in acetone. The reaction mixture was refluxed for 16 h. After cooling to ambient temperature, it was evaporated under reduced pressure to remove all the acetone. The residue was worked up using ethyl acetate and water, followed by a wash with brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a red oil (3.62 g, quant); 1H NMR (400 MHz, DMSO-d6): δ 2.12-2.19 (m, 2H); 3.24 (t, 2H, J=7.2 and 6.8 u Hz); 3.28 (s, 3H); 3.89 (t, 2H, J=6.8 Hz); 7.04-7.09 (m, 2H); 7.13-7.16 (m, 1H); 7.18-7.22 (m, 1H); MS for C11H13IN2O m/z 316.89 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customit was evaporated under reduced pressure
  3. customto remove all the acetone
  4. washa wash with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43788f393a8d49709fe3309f4384f0b8
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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