Sodium Azide → HCID 10405872, compound

HRID 2416152Notes

Reaction equation

HRID 2416152 reaction equation
I[CH2:2][C@H:3]([NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH2:4][C:5]([OH:7])=[O:6].[N-:19]=[N+:20]=[N-:21].[Na+]>CC#N.O>[CH2:14]([O:7][C:5](=[O:6])[CH2:4][C@@H:3]([NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH2:2][N:19]=[N+:20]=[N-:21])[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 69009828HCID 69009828, compound

Product 1

HCID 10405872HCID 10405872, compoundYield 196.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1 g of 5b (2.27 mmol) in 10 ml of CH3CN and 2 ml of water, NaN3 (0.592 g, 9.11 mmol) was added. The resulting suspension was stirred at 80° C. for 6 hours, then the solvent was removed under vacuum and the crude residue was diluted with water and extracted twice with ether. The organic layer was dried over anhydrous Na2SO4, and finally evaporated to obtain 0.790 g of crude product as a light yellow wax which was used without further purification with a yield of 98%;

Workup

  1. customthe solvent was removed under vacuum
  2. additionthe crude residue was diluted with water
  3. extractionextracted twice with ether
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customfinally evaporated

Sources & evidence

ORD record
ord-b58a0d2978fe42f2819e78b2050f5ffe
Source dataset
uspto-grants-2004_11
Patent number
US06822115B2

Reaction notes

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