Sodium Azide → HCID 19076487, compound

HRID 234483Notes

Reaction equation

HRID 234483 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH3:17])[CH:13]=2)[NH:8][C:7]1=[O:18]>C(#N)C>[N:1]([C:6]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH3:17])[CH:13]=2)[NH:8][C:7]1=[O:18])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19076605HCID 19076605, compound

Product 1

HCID 19076487HCID 19076487, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.339 g of sodium azide is added to a solution of 0.560 g of the compound obtained in step B or B' in 20 ml of acetonitrile and the mixture is refluxed for 30 minutes. The solvent is evaporated off under vacuum and the residue is taken up with water, extracted with AcOEt, washed with a saturated solution of NaCl, with water and with a 5% aqueous solution of sodium dithionite, re-extracted with DCM, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (95/5; v/v) as the eluent to give 0.377 g of the expected product. Infrared spectrum in DCM: 3440 cm-1, 2100 cm-1, 1745 cm-1.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. customThe solvent is evaporated off under vacuum
  3. extractionextracted with AcOEt
  4. washwashed with a saturated solution of NaCl, with water and with a 5% aqueous solution of sodium dithionite
  5. extractionre-extracted with DCM
  6. dry with materialdried over sodium sulfate
  7. customevaporated under vacuum
  8. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-8ea27f6095004d3eb803246a2c254649
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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