Sodium Azide → HCID 178510669, compound

HRID 1361035Notes

Reaction equation

HRID 1361035 reaction equation
C1(S([C:10](=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:11]#[N:12])(=O)=O)C=CC=CC=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:21]=[N:22][NH:23][C:10]=2[C:11]#[N:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 4277272HCID 4277272, compound

Product 1

HCID 178510669HCID 178510669, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzenesulfonyl-3-(4-hydroxyphenyl)acrylonitrile (2.08 g, 7.3 mmol) and sodium azide (0.47 g, 7.3 mmol) in DMF (50 mL) was heated at reflux temperature 2 hours. After cooling, the mixture was poured on ice. The mixture was evaporated in vacuo to almost dryness and toluene was added. After filtration, the organic phase was evaporated in vacuo. The residue was purified by silicagel chromatography eluting with a mixture of ethyl acetate and heptane (1:2). This afforded 1.2 g (76%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature 2 hours
  3. temperatureAfter cooling
  4. additionthe mixture was poured on ice
  5. customThe mixture was evaporated in vacuo to almost dryness and toluene
  6. additionwas added
  7. filtrationAfter filtration
  8. customthe organic phase was evaporated in vacuo
  9. customThe residue was purified by silicagel chromatography
  10. washeluting with a mixture of ethyl acetate and heptane (1:2)

Sources & evidence

ORD record
ord-a649736ff8054763ada958a258fd447b
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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