Water → 4-Azidobenzaldehyde

HRID 1358152

Reaction equation

HRID 1358152 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].O>CS(C)=O>[N:10]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 903854-Azidobenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

50 g 4-fluoro benzaldehyde and 50 g sodium azide were dispersed in 150 ml dry dimethyl sulfoxide. Subsequently, the mixture was heated for 3 hours at 105° C. while nitrogen was introduced. The mixture was poured into 200 ml water, and the solution extracted with 200 ml dichloro methane (three times). Then the solvent was distilled off by means of a vacuum rotation vaporizer. 53 g of a liquid remained having infrared (IR) and nuclear magnetic resonance (NMR) spectra consistent with the 4-azido benzaldehyde structure.

Workup

  1. additionwas introduced
  2. extractionthe solution extracted with 200 ml dichloro methane (three times)
  3. distillationThen the solvent was distilled off by means of a vacuum rotation vaporizer

Sources & evidence

ORD record
ord-83d9711f65f642a6b84fcbd04a7e823b
Source dataset
uspto-grants-2003_07
Patent number
US06596460B2

Linked notes

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