Sodium Iodide → HCID 19025822, compound

HRID 1033251Notes

Reaction equation

HRID 1033251 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1.[Br:13][CH2:14][CH2:15][CH2:16][S:17][CH2:18][CH2:19][CH2:20]Br.[I-].[Na+]>CCCCCC.CS(C)=O.CC(C)=O.C(OCC)(=O)C>[Br:13][CH2:14][CH2:15][CH2:16][S:17][CH2:18][CH2:19][CH2:20][N:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=[C:4]1[CH3:3]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 119842-MethylbenzimidazoleHCID 24758Sodium hydrideHCID 12557526HCID 12557526, compound

Product 1

HCID 19025822HCID 19025822, compoundYield 13.8%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Part A. Sodium hydride (0.11 g of 50% mineral oil suspension, 4.64 mmol) was washed with hexane, and dried under vacuum, then suspended in dimethylsulfoxide and cooled to 0° C. A solution of 2-methyl-1H-benzimidazole (0.61 g, 4.64 mmol) in dimethylsulfoxide (5 mL) was added dropwise. The ice bath was removed, and the mixture was allowed to stir for 5 hours. A solution of bis(3-bromopropyl)sulfide (Example 366, Part A; 2.56 g, 9.27 mmol) in dimethylsulfoxide (5 mL), along with sodium iodide (0.35 g, 2.32 mmol), were added, and the resulting mixture was heated to 80° C. for 20 hours. It was then cooled to ambient temperature, and poured into 100 mL ethyl acetate. This was washed with water (4×100 mL), and the aqueous phases were back-extracted in sequence with ethyl acetate (100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was separated by flash chromatography (1:1 ethyl acetatehexane, then ethyl acetate, then acetone) to afford 1-[3-(3-bromopropyl)thiopropyl]-2-methyl-1H-benzimidazole as an oil (0.21 g, 0.64 mmol). 1NMR (CDCl3): 7.74-7.23 (4H, m); 4.28 (2H, t, J=6 Hz); 3.52 (2H, t, J=6 Hz); 2.70 (2H, t, J=7 Hz); 2.66 (3H, s); 2.55 (2H, t, J=7 Hz); 2.19-2.02 (4H, m).

Workup

  1. customdried under vacuum
  2. customThe ice bath was removed
  3. temperaturethe resulting mixture was heated to 80° C. for 20 hours
  4. temperatureIt was then cooled to ambient temperature
  5. washThis was washed with water (4×100 mL)
  6. extractionthe aqueous phases were back-extracted in sequence with ethyl acetate (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was separated by flash chromatography (1:1 ethyl acetatehexane

Sources & evidence

ORD record
ord-dc807e94eee44382b1f88bf6263afb3b
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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