Sodium Azide → HCID 86608964, compound

HRID 1784667Notes

Reaction equation

HRID 1784667 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)OS1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[CH2:1]([NH:8][CH2:12][C@H:11]([N:21]=[N+:22]=[N-:23])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 67117402HCID 67117402, compound

Product 1

HCID 86608964HCID 86608964, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2RS,5S)-3-benzyl-5-(4-chlorophenyl)-1,2,3-oxathiazolidine 2-oxide (16.2 g, 52.6 mmol) and sodium azide (17.11 g, 263.2 mmol) in N,N-dimethylformamide (100 ml) was heated at 70° C. for 24 hours. The reaction mixture was partitioned between ether and water, and the organic layer was washed with water and brine successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10-20% ethyl acetate-hexane) to afford (R)-N-benzyl-2-azido-2-(4-chlorophenyl)ethylamine (12.7 g, 83.8%) as a yellow oil.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. washthe organic layer was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 10-20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c6eb2abc1f944a889777fbf03a22d6e7
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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