Sodium Iodide → HCID 178462744, compound

HRID 894371Notes

Reaction equation

HRID 894371 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[N:6]([CH2:10][CH3:11])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20].[I-:23].[Na+]>C(#N)C>[I-:23].[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[N+:6]([CH2:10][CH3:11])=[C:7]([CH3:9])[N:8]([CH2:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 75362(3-Chloropropyl)trimethylsilaneHCID 767171H-Benzimidazole, 5,6-dichloro-1-ethyl-2-methyl-

Product 1

HCID 178462744HCID 178462744, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5,6-Dichloro-1-ethyl-2-methylbenzimidazole (22.9 g, 0.10 moles), 3-chloropropyltrimethylsilane (15.0 g, 0.10 moles), and sodium iodide (15.0 g, 0.10 moles) were suspended in acetonitrile (200 ml) and with stirring the mixture was refluxed for 17 hours. It was filtered while hot to remove NaCl and the filtrate treated with ether (300 ml). Solid which precipitated was filtered off, washed with ether and dried. Yield 11.3 g (24%) mp 213°-5°. Additional crops were obtained by concentrating the filtrates and adding more ether. The mp of each crop was lower and less exact than the previous crop but all crops contained at least some product.

Workup

  1. temperaturewas refluxed for 17 hours
  2. filtrationIt was filtered while hot
  3. customto remove NaCl
  4. additionthe filtrate treated with ether (300 ml)
  5. customSolid which precipitated
  6. filtrationwas filtered off
  7. washwashed with ether
  8. customdried
  9. customAdditional crops were obtained
  10. concentrationby concentrating the filtrates
  11. additionadding more ether

Sources & evidence

ORD record
ord-6cc7515d86ad4403a2b4b30f1911139c
Source dataset
uspto-grants-1981_08
Patent number
US04283488

Reaction notes

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