Ammonium Chloride → HCID 91149373, compound

HRID 527965Notes

Reaction equation

HRID 527965 reaction equation
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[N-:14]=[N+:15]=[N-:16].[Na+].[NH4+].[Cl-]>CO>[N:14]([CH2:11][CH:9]([OH:10])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])[CH3:12])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

Product 1

HCID 91149373HCID 91149373, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-[2-[[(tert-butyl)dimethylsilyl]oxy]ethyl]-oxirane (5.0 g; prepared according to WO 2007/144423) in MeOH (150 mL) was reacted with NaN3 (3.95 g) and NH4Cl (2.37 g). The reaction mixture was further stirred at 80° C. overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between EA and water. The org. layer was washed with brine, dried over Na2SO4 and evaporated under reduced pressure, affording a yellow oil (4.9 g; 81% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EA and water
  3. washlayer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customaffording a yellow oil (4.9 g; 81% yield)

Sources & evidence

ORD record
ord-5ef31c27dfb5456fa122b914309889fa
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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