Ethanol → HCID 19815307, compound

HRID 653924Notes

Reaction equation

HRID 653924 reaction equation
[Na].[CH2:2]([O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][N:15]2[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][NH:17][C:16]2=[S:24])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH2:28][CH2:29][CH3:30].[CH2:31](O)C>>[CH2:2]([O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][N:15]2[C:19]([C:20]([O:22][CH2:23][CH3:31])=[O:21])=[CH:18][N:17]=[C:16]2[S:24][CH2:28][CH2:29][CH3:30])=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 336431-IodopropaneHCID 5360545Sodium2×HCID 19815370HCID 19815370, compound

Product 1

HCID 19815307HCID 19815307, compound

Procedure

To 60 mL of ethanol at 25° was added portionwise 0.30 g of sodium metal. After the sodium metal has reacted 3.54 g of 1-(4-benzyloxybenzyl)-5-carbomethoxy-2-(3H)-imidazolethione was added followed immediately by 2.24 mL of 1-iodopropane, and the mixture was stirred at 24° for 3 hours. At this point, the solvent was removed in vacuo, and the residue was dissolved in methylene chloride. This solution was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to furnish 3.46 g of crude 1-(4-benzyloxybenzyl)-2-propylthio-5-carboethoxyimidazole, used in a subsequent reaction without further purification; NMR (200 MHz, CDCl3): δ 7.77 (s, 1h); 7.45-7.32 (m, 5H); 7.03 (A2B2, 4H); 5.49 (s, 2H); 5.03 (s, 2H); 4.28 (quart., 2H); 3.20 (t, 2H); 1.32 (t, 3H); 1.02 (t, 3H).

Workup

  1. additionwas added
  2. customAt this point, the solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThis solution was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-baafc4fa87174aa48e7eddab16222d2a
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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