Sodium Azide → 5-Acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid

HRID 2383161Notes

Reaction equation

HRID 2383161 reaction equation
[C:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]2[N:9]=[C:10]([CH3:14])[O:11][C:12](=[O:13])[C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+]>C(O)(=O)C>[C:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([N:9]2[C:10]([CH3:14])=[N:19][N:18]=[N:17]2)=[C:7]([CH:6]=1)[C:12]([OH:11])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 46092582-Methyl-4-oxo-4H-benzo[d][1,3]oxazin-6-yl acetate

Product 1

HCID 670509905-Acetoxy-2-(5-methyltetrazol-1-yl)benzoic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-acetoxy-2-methylbenzo[d][1,3]oxazin-4-one (143 g, 0.653 mol) in 1.44 L of glacial acetic acid was stirred overnight with sodium azide (44.66 g, 0.687 mol). The solution was concentrated under reduced pressure and toluene (1.2 L) was then added. After stirring for one hour, a solid formed. The solid was recovered by filtration and then dried overnight under reduced pressure. The solid was dissolved in 2 L of water and the pH was adjusted to 1 with concentrated hydrochloric acid. After stirring for 3 hours, the resulting solid was filtered and dried overnight under a flow of air to give 164.1 g of 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid as an off white solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure and toluene (1.2 L)
  2. additionwas then added
  3. customa solid formed
  4. filtrationThe solid was recovered by filtration
  5. customdried overnight under reduced pressure
  6. dissolutionThe solid was dissolved in 2 L of water
  7. stirringAfter stirring for 3 hours
  8. filtrationthe resulting solid was filtered
  9. customdried overnight under a flow of air

Sources & evidence

ORD record
ord-34f934eb61f545a58dcbb53c6db52dd7
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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