Sodium Azide → HCID 118093152, compound

HRID 529860Notes

Reaction equation

HRID 529860 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:15])[CH:12](Br)[CH3:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.O>[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:15])[CH:12]([N:16]=[N+:17]=[N-:18])[CH3:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 52984174HCID 52984174, compound

Product 1

HCID 118093152HCID 118093152, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred a solution of N-(3-Acetylphenyl)-2-bromopropionamide (800 mg, 2.97 mmol) in DMF (10.0 mL) was added NaN3 (290 mg, 4.46 mmol). The reaction was stirred at room temperature under N2 atmosphere for 12 h, diluted with water, and the precipitated solid was filtered and dried to give the title product in 50% yield. 1H NMR (CDCl3, 400 MHz): 8.36 (br s, NH), 8.08-8.07 (m, 1H), 7.90-7.87 (m, 1H), 7.74-7.71 (m, 1H), 7.44 (t, J=8.0 Hz, 1H), 4.25 (q, J=6.8 Hz, 1H), 2.61 (s, 3H), 1.65 (d, J=6.8 Hz, 3H). 13C NMR (CDCl3, 100 MHz): 197.7, 168.2, 137.8, 137.5, 129.4, 124.6, 124.5, 119.5, 59.4, 26.7, 17.1. ESI-MS calcd for C11H11N4O2 (M−H)+231.09. found 231.1.

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-28d13c3bb22f4f6fabf7cc853df5a99c
Source dataset
uspto-grants-2016_05
Patent number
US09347948B2

Reaction notes

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