Imidazole → HCID 57581112, compound

HRID 1982948Notes

Reaction equation

HRID 1982948 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8]O)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[C:16]([Si:19]([CH3:21])([CH3:20])[CH2:8][CH2:7][O:6][C:5]1[CH:10]=[CH:11][C:2]([NH2:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)([CH3:18])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 148519Ethanol, 2-(4-amino-3-nitrophenoxy)-

Product 1

HCID 57581112HCID 57581112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-amino-3-nitro-phenoxy)-ethanol Compound 18a (0.5 g, 2.52 mmol) was treated with TBSCl (0.42 g, 2.52 mmol) and imidazole (0.173 g, 2.52 mmol) in DMF (10 mL) at room temperature overnight. DMF was removed under vacuum and the residue was diluted with AcOEt, washed with H2O and saturated aqueous NH4Cl and dried over Na2SO4. The solvent was evaporated to dryness to provide 4-[2-(tert-butyl-dimethyl-silanyl)-ethoxy]-2-nitro-phenylamine Compound 18b (0.787 g) as a golden solid. LCMS single peak, 3.93 min, MS (ESI) m/z 313.2 (M+H+). 1H NMR (300 MHz, CDCl3) δ 7.46 (s, 1 H), 7.00 (d, 1 H, J=9.0 Hz), 6.66 (d, 1 H, J=9.0 Hz), 3.94-3.84 (m, 4 H), 0.81 (s, 9 H), −0.01 (s, 6 H).

Workup

  1. customDMF was removed under vacuum
  2. additionthe residue was diluted with AcOEt
  3. washwashed with H2O and saturated aqueous NH4Cl
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-becedf3a162a4f6994eadaa3d62fe433
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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