Sodium Azide → 3-Azido-1-benzhydrylazetidine

HRID 323604Notes

Reaction equation

HRID 323604 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[N:29]([CH:16]1[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15]1)=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 155126511-Benzhydrylazetidin-3-yl 4-methylbenzenesulfonate

Product 1

HCID 155126523-Azido-1-benzhydrylazetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9 (11.5 g, 31.8 mmol) and sodium azide (4.12 g, 64 mmol) in 250 ml of DMF was heated to 70° C. for 24 hours. After cooling to room temperature the solvent was removed in vacuo and the residue partitioned between chloroform and water. The organics were dried over MgSO4, filtered and the solvent removed in vacuo. The crude product was purified by chromatography on silica gel (8:1 hexane: ethyl acetate) afforded the title compound.

Workup

  1. customwas removed in vacuo
  2. customthe residue partitioned between chloroform and water
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe crude product was purified by chromatography on silica gel (8:1 hexane: ethyl acetate)

Sources & evidence

ORD record
ord-b1217393730944209c1603dc36d443ea
Source dataset
uspto-grants-2001_04
Patent number
US06214832B1

Reaction notes

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