Imidazole → HCID 58056204, compound

HRID 1773572Notes

Reaction equation

HRID 1773572 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[C:12]([N+:23]([O-:25])=[O:24])[CH:11]=1.N1C=CN=C1>CN(C)C=O>[C:1]([Si:5]([O:22][C:18]1[CH:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][C:12]=2[N+:23]([O-:25])=[O:24])[CH:21]=[CH:20][CH:19]=1)([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58056317HCID 58056317, compound

Product 1

HCID 58056204HCID 58056204, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylchlorosilane (0.82 g, 5.44 mmol) was added at room temperature to a solution of 4′-chloro-2′-nitro-biphenyl-3-ol (1.05 g, 4.21 mmol) and imidazole (0.58, 8.52 mmol) in anhydrous N,N-dimethylformamide (30 mL) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was then partitioned between water and ethyl acetate, the organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (hexane/EtOAc, 90/10) to give 1.43 g (94% yield) of tert-butyl-(4′-chloro-2′-nitro-biphenyl-3-yloxy)-dimethyl-silane as a yellow oil.

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified on a silica gel plug (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-fcc9bd202f71423aa1f23029510a4101
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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