Chlorotrimethylsilane → 1-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

HRID 1032333Notes

Reaction equation

HRID 1032333 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][OH:13])[N:7]=[CH:6]1)=[O:4].C(N(CC)CC)C.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C(#N)C.CCOCC>[CH3:14][N:2]([CH3:1])[C:3]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:7]=[CH:6]1)=[O:4]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 145750511-Dimethylcarbamoyl-4-(3-hydroxypropyl)-imidazole

Product 1

HCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1-Dimethylcarbamoyl-4-(3-hydroxypropyl)-imidazole (19.8 g, 0.10 mole) and triethylamine (15 g, 0.15 mole) are dissolved in acetonitrile (100 mL) and the solution is stirred and cooled in an ice bath during the dropwise addition of chlorotrimethylsilane (11.9 g, 0.11 mole). The reaction is stirred at ice-bath temperature for 1 hour and is subsequently allowed to stand at ambient temperature for 15 hours. The mixture is diluted with ether (500 mL), filtered, and the solvent is evaporated to give 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole as an oil; NMR (imidazole protons): 2.2 (s) and 3.05 (s) ppm.

Workup

  1. stirringThe reaction is stirred at ice-bath temperature for 1 hour
  2. filtrationfiltered
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-7cfb334db5824ce4b6073ad9f6ea7411
Source dataset
uspto-grants-1990_09
Patent number
US04957931

Reaction notes

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