Ethyl orthoformate → methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

HRID 1601428Notes

Reaction equation

HRID 1601428 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH:14]=[N:26][N:25]=[N:24]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 89843Methyl 5-amino-o-anisate

Product 1

HCID 18464873methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Combine methyl 2-methoxy-5-aminobenzoate (3.94 g, 21.7 mmol) and triethyl orthoformate (12.8 g, 86.7 mmol) in glacial acetic acid (20 mL). After 20 hours, concentrate the reaction mixture in vacuo to remove ethanol. Add glacial acetic acid (20 mL) and sodium azide (5.64 g, 86.7 mmol). Heat to 70° C. After 1 hour, add glacial acetic acid (10 mL) and continue to heat to 70° C. After an additional hour, cool the reaction mixture to ambient temperature, dilute with water (500 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate.

Workup

  1. concentrationconcentrate the reaction mixture in vacuo
  2. customto remove ethanol
  3. waitAfter 1 hour
  4. temperatureto heat to 70° C
  5. waitAfter an additional hour
  6. temperaturecool the reaction mixture to ambient temperature
  7. customCollect the solid
  8. filtrationby filtration
  9. washrinse with water
  10. customdry

Sources & evidence

ORD record
ord-c4d928f44a684a2ebc128f0e160eaf9a
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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