Sodium Azide → 3-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester

HRID 1422409Notes

Reaction equation

HRID 1422409 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:7]([C:8]([NH:10][CH3:11])=O)[CH:6]=1)[CH3:2].S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:7]([C:8]2[N:10]([CH3:11])[N:36]=[N:35][N:34]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 47099901N-Methyl-5-nitro-isophthalamic acid ethyl ester

Product 1

HCID 667334013-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl esterYield 59.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

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).

Workup

  1. stirringstirred overnight
  2. customthe organic and aqueous layers were separated
  3. customthe organic layer dried
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-7569141930704fabb34a23bc156c6349
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

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