Tert-Butyl nitrite → tert-Butyl 4-azido-3-iodobenzylcarbamate

HRID 1961487Notes

Reaction equation

HRID 1961487 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17].N(OC(C)(C)C)=O.[Si]([N:29]=[N+:30]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate

Product 1

HCID 86661980tert-Butyl 4-azido-3-iodobenzylcarbamateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-amino-3-iodobenzylcarbamate (1.0 g, 2.87 mmol) was dissolved in CH3CN (6.0 ml). The solution was cooled to 0° C., tert-butyl nitrite (444.3 mg, 4.30 mmol) and TMS azide (397.1 mg, 3.45 mmol) were added. The mixture was then stirred at r.t for 2.0 h. The solvents were removed under vacuum and the residue purified by flash chromatography (Pet. Ether/EtOAc 85:15) affording 936 mg (87%) of the title compound.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue purified by flash chromatography (Pet. Ether/EtOAc 85:15)

Sources & evidence

ORD record
ord-f1d7edcee4fb4b16bc6067874f8b8fdd
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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