Ethyl Acetate → 1-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-ethanone

HRID 500528Notes

Reaction equation

HRID 500528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[C:11]([CH:13]=[CH:14]C3C=CC=CC=3)[NH:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.CC[O:23]C(C)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:9]=[N:10][C:11]([C:13](=[O:23])[CH3:14])=[N:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl Acetate2×HCID 178478134HCID 178478134, compound

Product 1

HCID 248533891-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-ethanoneYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of Example 10.1 (1.50 g, 5.06 mmol) was dissolved in dichloromethane (79 mL) and ozone was bubbled through the solution for a period of 15 minutes. The solution turned from orange to a darker orange colour. The reaction completeness was checked using a 10% EtOAc:hexanes TLC solvent system. Oxygen was bubbled through the solution for an additional 5 minutes to remove any excess ozone remaining. Dimethyl sulfide (5 mL) was added to the solution and the mixture was allowed to equilibrate to room temperature. The solvent was removed under vacuum and an oily brown substance remained. A 3 cm flash column was prepared containing 15 cm silica and ˜3 cm sand. The column was run using a 5% EtOAc:hexanes solvent system. The eluted fractions containing the product were collected and concentrated under low pressure. Flash column chromatography (silica, 5% EtOAc:hexanes) yielded 893 mg (79.4% yield) of the title compound.

Workup

  1. customozone was bubbled through the solution for a period of 15 minutes
  2. customOxygen was bubbled through the solution for an additional 5 minutes
  3. customto remove any excess ozone remaining
  4. additionDimethyl sulfide (5 mL) was added to the solution
  5. customto equilibrate to room temperature
  6. customThe solvent was removed under vacuum
  7. customA 3 cm flash column was prepared
  8. additioncontaining 15 cm silica and ˜3 cm sand
  9. additionThe eluted fractions containing the product
  10. customwere collected
  11. concentrationconcentrated under low pressure

Sources & evidence

ORD record
ord-9207402b217041c793c9cd1f8ad9f31f
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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