Sodium Azide → HCID 57418743, compound

HRID 1897430Notes

Reaction equation

HRID 1897430 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[C:7](F)=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10]>CC(N(C)C)=O.O.CCOCC>[N:1]([C:11]1[CH:12]=[CH:13][C:6]([F:5])=[CH:7][C:8]=1[C:9]#[N:10])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 889352,3-Difluorobenzonitrile

Product 1

HCID 57418743HCID 57418743, compoundYield 102.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of NaN3 (1.17 g, 1.8 mmol) and difluorobenzonitrile (0.5 g, 3.6 mmol) in DMA (60 mL) was heated at 100° C. for 30 minutes. The mixture was next diluted with water (300 mL) and ether (300 mL). The organic layer was washed three times with water and brine. The organic layer was dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography using ether:hexane (1:5) as eluent to give the desired product (1q) as white crystals (0.3 g, 53% isolated yield). 1H NMR (400 MHz, CDCl3) δ 7.38-7.31 (m, 2H), 7.27-7.18 (m, 1H).

Workup

  1. washThe organic layer was washed three times with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-5e3a0cdf53914d5cb71499c219ff2b8c
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

Loading…