Triethylamine → HCID 178455170, compound

HRID 993032Notes

Reaction equation

HRID 993032 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.C(N(CC)CC)C.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>ClCCl.CN(C=O)C>[Si:20]([O:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418488HCID 178418488, compound

Product 1

HCID 178455170HCID 178455170, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Hydroxymethylimidazole hydrochloride (5.03 g) was dissolved in a mixed solvent of dichloromethane (90 mL) and DMF (20 mL), and to the solution triethylamine (8.25 g) was added at 0° C. tert-Butyldimethylchlorosilane (6.14 g) was then added to the mixture, and the resultant mixture was stirred at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound.

Workup

  1. additionwas then added to the mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was then purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-a1f1bbdabcd143f2add094db40d5c5c5
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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