Reaction #1509591

ord-7569141930704fabb34a23bc156c6349

Reaction equation

[N-]=[N+]=[N-].[Na+]
sodium azide
CCOC(=O)c1cc(C(=O)NC)cc([N+](=O)[O-])c1
N-methyl-5-nitro-isophthalamic acid ethyl ester
O=C([O-])O.[Na+]
NaHCO3
O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
triflic anhydride
→
CCOC(=O)c1cc(-c2nnnn2C)cc([N+](=O)[O-])c1
title compound
Yield 59.1%
CCOC(=O)c1cc(-c2nnnn2C)cc([N+](=O)[O-])c1
3-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester
Yield 59.1%

Reactants

[N-]=[N+]=[N-].[Na+]
sodium azide
—
solution
CCOC(=O)c1cc(C(=O)NC)cc([N+](=O)[O-])c1
N-methyl-5-nitro-isophthalamic acid ethyl ester
O=C([O-])O.[Na+]
NaHCO3
O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
triflic anhydride

Reagents

None

Solvents

CC(Cl)Cl
dichloroethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGstirred overnight
  2. 2
    Otherthe organic and aqueous layers were separated
  3. 3
    Otherthe organic layer dried
  4. 4
    Concentrationconcentrated in vacuum

Procedure

To a 2M solution of N-methyl-5-nitro-isophthalamic acid ethyl ester (10 g) in dichloroethane (200 ml) at −20° C. was added pre-cooled triflic anhydride (10 ml) dropwise. This was stirred for 30 min and then sodium azide (4.6 g) was added. This was allowed to warm to room temperature and stirred overnight. The reaction was neutralised with 5% NaHCO3 (aq) solution and the organic and aqueous layers were separated and the organic layer dried and concentrated in vacuum. Flash chromatography (100:0 to 50:50 gradient cyclohexane:EtOAc) afforded the title compound (6.5 g). Rt=1.52 min (method D).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045323E1uspto-grants-2015_01