Sodium Azide → HCID 22097685, compound

HRID 1458953Notes

Reaction equation

HRID 1458953 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]Cl)=[CH:3][CH:2]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CS(C)=O.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][N:11]=[N+:12]=[N-:13])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 2054424-(3-Chloropropyl)pyridine

Product 1

HCID 22097685HCID 22097685, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2-3 (7 g, 41.2 mmol) in DMSO (150 mL) was treated with sodium azide (2 g, 45.3 mmol) and heated to 65° C. for 72 h. The solution was diluted with EtOAc, washed with H2O and saturated NaHCO3. The H2O washing was basified to pH11 and extracted with EtOAc. The organic layers were combined, dried with brine and MgSO4, filtered and evaporated to give 2-4 as a yellow oil.

Workup

  1. washwashed with H2O and saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried with brine and MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-92fdad09ba7942e7b1ae74fe88199c19
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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