Hydrogen iodide → HCID 18465001, compound

HRID 2230738Notes

Reaction equation

HRID 2230738 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH:20]=[CH2:21])[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[IH:26]>CO>[IH:26].[IH:26].[N:11]1([C:15]2[N:19]([CH:20]=[CH2:21])[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[N:16]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 24841Hydrogen iodide2×HCID 70148112HCID 70148112, compound

Product 1

HCID 18465001HCID 18465001, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a stirred solution of 4-(1-vinyl-1H-benzoimidazol-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.97 g, 2.8 mmol) and methanol (20 mL) at 0° C. with 57% hydroiodic acid (467 microliters, 6.21 mmol) solution. Stir at room temperatue for two hours, add 57% hydroiodic acid (934 microliters) and reflux for 30 minutes. Cool to room temperature, concentrate in vacuo to approximately 5 mL final volume, and add ether (total of 200 mL) to afford a tacky solid. Stir the suspension overnight, collect the solid by filtration under nitrogen and dry in vacuo for two hours. Dry in vacuo (0.2 Torr) at room temperature overnight to afford 1.33 g of 2-[1,4]diazepan-1-yl-1-vinyl-1H-benzoimidazole dihydroiodide.

Workup

  1. temperaturereflux for 30 minutes
  2. concentrationconcentrate in vacuo to approximately 5 mL final volume
  3. additionadd ether (total of 200 mL)
  4. customto afford a tacky solid
  5. stirringStir the suspension overnight
  6. customcollect the solid
  7. filtrationby filtration under nitrogen
  8. customdry in vacuo for two hours
  9. customDry in vacuo (0.2 Torr) at room temperature overnight

Sources & evidence

ORD record
ord-ed82fa423a624a27af3b663f73259f84
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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