Azidotrimethylsilane → HCID 59327682, compound

HRID 541008Notes

Reaction equation

HRID 541008 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Si]([N:23]=[N+:24]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:7]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 458884N-(4-Aminophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 59327682HCID 59327682, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Following the procedure of Moses and coworkers (K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett. 2007, 9, 1809-1811). N-(4-aminophenyl)-4-methylbenzene-1-sulfonamide (1.00 g, 3.81 mmol) was dissolved in anhydrous CH3CN (6 mL), and the resulting solution was placed under Ar(g) and cooled to 0° C. To this was added t-BuONO (0.68 mL, 5.71 mmol) followed by TMSN3 (0.60 mL, 4.57 mmol) dropwise. The resulting solution was allowed to warm to room temperature and stirred for 2 h. The resulting mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexanes, to give aryl azide 7 (1.02 g, 3.54 mmol, 93% yield) as a white solid.

Workup

  1. additionTo this was added t-BuONO (0.68 mL, 5.71 mmol)
  2. temperatureto warm to room temperature
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-5bb4230233584840a36f420a27b6aea8
Source dataset
uspto-grants-2014_10
Patent number
US08871916B2

Reaction notes

Loading…