Ethyl orthoformate → Benzeneacetic acid, 3-iodo-4-(1H-tetrazol-1-yl)-, methyl ester

HRID 2173406Notes

Reaction equation

HRID 2173406 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[I:13].[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[I:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[N:1]1[CH:14]=[N:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 46941390Methyl (4-amino-3-iodophenyl)acetate

Product 1

HCID 86693029Benzeneacetic acid, 3-iodo-4-(1H-tetrazol-1-yl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl (4-amino-3-iodophenyl)acetate (5 g, 17.2 mmol) and triethyl orthoformate (7.6 mg, 51.5 mmol) in 40 mL of HOAc was added sodium azide (1.2 g, 17.2 mmol), and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford methyl [3-iodo-4-(1H-tetrazol-1-yl)phenyl]acetate. 1H-NMR (300 MHz, CDCl3) δ ppm 8.90 (s, 1H), 7.96 (s, 1H), 7.47 (d, J=8.2 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 3.74 (s, 3H), 3.70 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatograph

Sources & evidence

ORD record
ord-13077a9541fd4373abbc209cbb703eae
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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