Sodium Azide → HCID 15220953, compound

HRID 1608959Notes

Reaction equation

HRID 1608959 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12](C(O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])C(Cl)=O.[N-:24]=[N+]=[N-].[Na+].[C:28]1([CH:34]2[CH:38]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[NH:37][NH:36][C:35]2=[O:45])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:24][C:18]([N:37]2[CH:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:34]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:35](=[O:45])[NH:36]2)=[O:22])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acidHCID 2704924,5-diphenyltetrahydro-3h-pyrazol-3-one

Product 1

HCID 15220953HCID 15220953, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-Benzyloxybenzoic acid (2.0 g, 8.8 mmol was suspended in 50 mL toluene with oxalyl chloride (5 mL) and heated to reflux for 15 min. Solvent was removed in vacuo, the residue redissolved in 30 mL acetone, and an aqueous solution of NaN3 (1.16 g, 17.6 mmol, 2.0 eq. in 10 mL H2O) added dropwise with external cooling by a water bath. The mixture was stirred for 1 hour, diluted with H2O, extracted twice with toluene, then the combined extracts washed with water and brine, and dried over Na2SO4. This solution of acyl azide was treated with 4,5-diphenyl-3-pyrazolidinone (1.6 g, 6.8 mmol, 0.76 eq.), warmed until bubbles evolved, and heating maintained for 30 min. After stirring overnight at room temperature, the solvent was removed in vacuo, and the product isolated by chromatography (0-30% EtOAc:hexane gradient) as 1.6 g (52%) white solid: mp 127°-30° C.;

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 min
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue redissolved in 30 mL acetone
  5. temperaturewith external cooling by a water bath
  6. extractionextracted twice with toluene
  7. washthe combined extracts washed with water and brine
  8. dry with materialdried over Na2SO4
  9. temperaturewarmed until bubbles
  10. temperatureheating
  11. temperaturemaintained for 30 min
  12. stirringAfter stirring overnight at room temperature
  13. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-41f9d838e63142f4b15332234043c424
Source dataset
uspto-grants-1995_03
Patent number
US05399565

Reaction notes

Loading…