Sodium Iodide → HCID 18956332, compound

HRID 2379898Notes

Reaction equation

HRID 2379898 reaction equation
[CH:1]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)([CH3:3])[CH3:2].Br[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I-].[Na+].C(OCC)(=O)C>CN(C)C=O>[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=[C:4]1[CH:1]([CH3:3])[CH3:2])([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 221212-(propan-2-yl)-1H-1,3-benzodiazoleHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 18956332HCID 18956332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A. Sodium hydride (1.62 g of a 50% slurry, 33.8 mmol) was washed with hexane and dried under vacuum. Dimethylformamide (50 mL) was added, followed by a solution of 2-isopropyl-1H-benzimidazole (5.41 g, 33.8 mmol) in dimethylformamide (15 mL). After stirring at ambient temperature for two hours, the mixture was treated with ethyl 5-bromovalerate (5.50 mL, 34.8 mmol) and sodium iodide (1.19 g, 7.94 mmol). The mixture was heated to 80° C. for 18 hours, then cooled and poured into ethyl acetate (200 mL). This was washed with water (4×200 mL), then brine (200 mL), and dried over anhydrous magnesium sulfate, filtered and evaporated. The product, 1-(4-carboethoxybutyl)-2-(1-methylethyl)-1H-benzimidazole, was obtained as an oil after purification by silica gel chromatography (1:2 ethyl acetate-hexane) (9.54 g, 33.1 mmol, 98%). 1H NMR (CDCl3): 7.75 (1H, dd, J= 5.6, 3.1 Hz); 7.34-7.19 (3H, m); 4.12 (2H, q, J=7.1 Hz); 1.92-1.80 (2H, m); 1.78-1.65 (2H, m); 1.45 (6H, d, J=6.6 Hz); 1.24 (3H, t, J=7.0 Hz).

Workup

  1. washSodium hydride (1.62 g of a 50% slurry, 33.8 mmol) was washed with hexane
  2. customdried under vacuum
  3. additionDimethylformamide (50 mL) was added
  4. temperatureThe mixture was heated to 80° C. for 18 hours
  5. temperaturecooled
  6. washThis was washed with water (4×200 mL)
  7. dry with materialbrine (200 mL), and dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-cbd1b5e6f7d448f4bd33ae3dc07b841d
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

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