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

HRID 637169Notes

Reaction equation

HRID 637169 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:13]=[N:25][N:24]=[N:23]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 15049977Methyl 5-Amino-2-methylbenzoate

Product 1

HCID 18464615methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70° C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

Workup

  1. waitAfter 2 hours
  2. temperaturecool the reaction mixture to ambient temperature
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with water
  6. customdry

Sources & evidence

ORD record
ord-33257545030f42228177537b8f9ec6b5
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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