Sodium Azide → HCID 57271412, compound

HRID 1418366Notes

Reaction equation

HRID 1418366 reaction equation
[CH2:1]1[O:24][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:11][CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[O:3][CH2:2]1.[N-:25]=[N+:26]=[N-:27].[Na+]>CS(C)=O.O>[CH2:1]1[O:24][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:11][CH2:12][N:25]=[N+:26]=[N-:27])[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57061434HCID 57061434, compound

Product 1

HCID 57271412HCID 57271412, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-(2-(4-methylphenylsulphonyloxy)ethyl)benzaldehyde ethylene acetal (1.43 g, 4.10 mmol) and sodium azide (0.53 g, 8.2 mmol) in DMSO (20 ml) was stirred for 16 h, diluted with water, extracted three times with ether, washed with brine, dried over sodium sulphate and evaporated to afford the product as a yellow oil (0.86 g), MS (+EI) 190 [(M-NH2)+], 1H NMR (d6 -DMSO) 7.53-7.25 (4H, m), 5.92 (1H, s), 4.19-3.95 (4H, m), 3.53 (2H, t, J7.2 Hz), 2.98 (2H, t, J7.2 Hz).

Workup

  1. extractionextracted three times with ether
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-b21bbf11d64d4472bf59610d117ab15b
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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