Sodium Azide → HCID 19359208, compound

HRID 1417912Notes

Reaction equation

HRID 1417912 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[CH:8]=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:20]([CH2:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:16]([O:18][CH3:19])=[O:17])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 19359167HCID 19359167, compound

Product 1

HCID 19359208HCID 19359208, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Carbomethoxy-5-nitrobenzyl methanesulfonate (300.0 g, 1.04 mol) and sodium azide (81.0 g, 1.25 mol) were suspended in DMF (1700 ml) and stirred at room temperature for 5 hours. The reaction was diluted with ethyl acetate (2000 ml), washed with 1000 ml portions of H2O (2×) and saturated NaCl (1×), dried (MgSO4), and concentrated under reduced pressure. The resulting amber syrup was dried under vacuum at 40° C. to yield the title compound as a tan solid (226.5 g, 92%). 1H NMR (CDCl3): 8.60 (s, 1H), 8.26 (s, 1H), 8.20 (s, 1H), 4.52 (s, 2H), 3.88 (s, 3H); MP=44°-46° C.

Workup

  1. washwashed with 1000 ml portions of H2O (2×) and saturated NaCl (1×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting amber syrup was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-1403b2f6f09449c8a38cb7d05932a2de
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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