Pyridine → HCID 86674907, compound

HRID 589177Notes

Reaction equation

HRID 589177 reaction equation
[NH2:1][O:2][Si:3]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].N1C=CC=CC=1.[C:16](Cl)(=[O:27])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>ClC(Cl)C.ClCCl>[Si:3]([O:2][NH:1][C:16](=[O:27])[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamine

Product 1

HCID 86674907HCID 86674907, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 63651,1-DichloroethaneSolvent2×

Procedure

(Aminooxy) (tert-butyl)dimethylsilane (1.00 g, 6.79 mmol) was dissolved in a mixture of dry pyridine (0.549 mL, 6.79 mmol) and dichloroethane (15 mL; dichloromethane could also be used), and a solution of 4-nitrophenyl chlorocarbonate (1.37 g, 6.79 mmol) in dichloroethane (7 mL) was added over 5 min. The resulting mixture was stirred at room temperature overnight and was then diluted with dichloromethane, washed twice with water, twice with saturated aqueous sodium bicarbonate, and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by chromatography (90 g silica gel, 20% EtOAc/hexanes eluent) to give the title compound (1.73 g, 81%) as a white solid.

Workup

  1. additionwas added over 5 min
  2. washwashed twice with water, twice with saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography (90 g silica gel, 20% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-79278e77beb24cff89cf649a0ccf734a
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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