Imidazole → 2-[4-(Tert-butyldimethylsilanyloxy)-3-chlorophenyl]acetamide

HRID 6726Notes

Reaction equation

HRID 6726 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C)C=O.C(OCC)(=O)C>[Si:18]([O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][C:10]([NH2:12])=[O:11])=[CH:3][C:2]=1[Cl:1])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 150383753-Chloro-4-hydroxyphenylacetamide

Product 1

HCID 220185072-[4-(Tert-butyldimethylsilanyloxy)-3-chlorophenyl]acetamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(3-chloro-4-hydroxy-phenyl)-acetamide (100 mg), imidazole (184 mg), and tert-butyldimethylsilyl chloride (163 mg) was stirred for 2 h in 5 mL of dimethylformamide. The solution was diluted with 50 mL of ethyl acetate and washed with 50 mL of sodium carbonate. The ethyl acetate was evaporated to afford 125 mg of 2-[4-(tert-butyldimethylsilanyloxy)-3-chlorophenyl]acetamide.

Workup

  1. washwashed with 50 mL of sodium carbonate
  2. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-2e6609cbcbab46a8a867933955519b54
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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