Imidazole → HCID 69548567, compound

HRID 641730Notes

Reaction equation

HRID 641730 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11]N1C(C)=CN=C1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[CH2:23](Cl)Cl>O>[Si:1]([O:9][CH2:10][CH2:11][C:19]1[NH:18][C:22]([CH3:23])=[CH:21][N:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 11557283HCID 11557283, compound

Product 1

HCID 69548567HCID 69548567, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyldimethylsilyl chloride (9.05 g) was added to a stirred mixture of 1-(2-hydroxyethyl)-5-methylimidazole (6.4 g), imidazole (7.5 g) and methylene chloride (30 ml) which was cooled to 0° C. The reaction mixture was stirred at ambient temperature for 4 hours. The mixture was poured into water. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give 1-(2-(tert-butyldimethylsilyloxyethyl)-5-methylimidazole (11.7 g); NMR Spectrum: (CDCl3)-0.04 (s, 6H), 0.85 (s, 6H), 2.2 (s, 3H), 3.8 (m, 2H), 3.94 (m, 2H), 6.75 (s, 1H), 7.43 (s, 1H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-2d230c1c31ed4aa88496190c41424540
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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