Imidazole → HCID 54110739, compound

HRID 654872Notes

Reaction equation

HRID 654872 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].N1C=CN=C1.[CH3:11][C@H:12]([CH2:28][CH3:29])[C@:13]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([OH:20])[CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1.O>CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@:13]([O:20][Si:2]([CH3:4])([CH3:3])[CH3:1])([C@H:12]([CH3:11])[CH:28]=[CH2:29])[CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 53766196HCID 53766196, compound

Product 1

HCID 54110739HCID 54110739, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2.47 ml (19.4 mmole) of trimethylsilyl chloride and 1.7 g (24.3 mmole) of imidazole were added to a solution of 900 mg (3.24 mmole) of (2R*,3R*)-3-methyl-2-(4-chlorophenyl) -(1H-1,2,4-triazol-1-yl)-2-pentanol in 20 ml of N,N-dimethylformamide, and then the mixture was stirred at 50° C. for 4 hours. At the end of this time, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure to give 1.3 g of the title compound in the form of a crude oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1f26f3a66ef24f7c803af4eb8b4116aa
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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