Acetic Acid → HCID 57312355, compound

HRID 1809161Notes

Reaction equation

HRID 1809161 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C(O)(=O)C.[CH:15](OCC)(OCC)OCC.[N-:25]=[N+:26]=[N-:27].[Na+].Cl.N([O-])=O.[Na+]>O>[N:1]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])[CH:15]=[N:27][N:26]=[N:25]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 16453-AminobenzamideHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 57312355HCID 57312355, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottom flask was added 3-aminobenzamide (1.36 g, 10.0 mmol, 1.0 eq.), acetic acid (9.1 mL, 160 mmol, 16.0 eq.), triethyl orthoformate (5.4 mL, 32.0 mmol, 3.2 eq.), and sodium azide (0.812 g, 12.5 mmol, 1.25 eq.). The reaction mixture was then heated to 80° C. until all solids were dissolved. The reaction was stirred at 80° C. for an additional 2 h before cooling to RT. Water (6.0 mL,) was added, followed by 6N HCl (5.3 mL), and then 25% NaNO2 (2.1 mL). The resulting precipitate was filtered and rinsed with water to give pure tetrazole 38 (1.5 g, 80% yield). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 189.9 (M+H)+1, 187.9 (M−H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.1 (s, 1H), 8.39 (t, 1H), 8.20 (br. s, 1H), 8.05 (m, 2H), 7.72 (t, 1H), 7.55 (s, 1H) ppm.

Workup

  1. dissolutionwere dissolved
  2. temperaturebefore cooling to RT
  3. filtrationThe resulting precipitate was filtered
  4. washrinsed with water

Sources & evidence

ORD record
ord-f863b46ed13f48d0b3d429146887c40d
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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