Azidotrimethylsilane → HCID 59327682, compound

HRID 1803044Notes

Reaction equation

HRID 1803044 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-6561ea64836d4ac1a9c1671ee5d4c7b6
Source dataset
uspto-grants-2013_01
Patent number
US08350014B2

Reaction notes

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