Imidazole → HCID 15199977, compound

HRID 1756824Notes

Reaction equation

HRID 1756824 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.CN(C=O)C>O>[Si:18]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1380892HCID 1380892, compound

Product 1

HCID 15199977HCID 15199977, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL flask, equipped with magnetic stirrer and septum, was charged with 16.6 g crude 16 (0.095 mole), 22.1 g TBDMS-Cl (97%, 0.142 mole), 13.1 g imidazole (99%, 0.19 mole) and 240 mL DMF (distilled, added by syringe). The mixture was stirred under argon for 8 hours and then poured into 1.0 L of water and extracted with ether (3×450 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give 36.4 g of crude (orange solid). Crystallization from Et2O-pentane (1:9) and chromatography of the mother liquor concentrate on silica gel (Et2O-pentane 1:2) gave 25.0 g of 17, 91% yield.

Workup

  1. customA 500 mL flask, equipped with magnetic stirrer
  2. extractionextracted with ether (3×450 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give 36.4 g of crude (orange solid)
  7. customCrystallization from Et2O-pentane (1:9) and chromatography of the mother liquor
  8. concentrationconcentrate on silica gel (Et2O-pentane 1:2)

Sources & evidence

ORD record
ord-7bfb6dbb15b3416cbec80d3ae8156480
Source dataset
uspto-grants-1995_08
Patent number
US05442065

Reaction notes

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