Sodium Azide → HCID 89996091, compound

HRID 1480867Notes

Reaction equation

HRID 1480867 reaction equation
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[C:21]([NH:23][CH3:24])=O.[N-:31]=[N+:32]=[N-:33].[Na+].C([O-])(O)=O.[Na+]>CC#N>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:21]2[N:23]([CH3:24])[N:33]=[N:32][N:31]=2)[CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 568324173-Methoxy-N-methyl-4-nitrobenzamide

Product 1

HCID 89996091HCID 89996091, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triflic anhydride (0.27 mL, 1.580 mmol) was added dropwise to a solution of 3-methoxy-N-methyl-4-nitrobenzamide (Preparation 196, 0.166 g, 0.790 mmol) and sodium azide (0.205 g, 3.16 mmol) in MeCN (4.0 mL) at −10° C. The reaction mixture was warmed up to room temperature over 3 hours. The reaction was neutralised with saturated aqueous NaHCO3. The mixture was extracted with EtOAc and the organic layer washed with saturated aqueous NaHCO3, brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with cyclohexane/EtOAc 70/30 to 50/50 to afford the title compound as a white solid (129 mg, 69%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic layer washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage silica gel column chromatography
  7. washeluting with cyclohexane/EtOAc 70/30 to 50/50

Sources & evidence

ORD record
ord-bd794829de96476a83ddb265f8667044
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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