Sodium hydride → methyl 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoate

HRID 323412Notes

Reaction equation

HRID 323412 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.CNC=O.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>CN(C)C=O.ClCCl.CO>[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]([CH2:24][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 31254N-MethylformamideHCID 240622Methyl 5-(chloromethyl)-2-methoxybenzoateHCID 178418936HCID 178418936, compound

Product 1

HCID 18464866methyl 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Combine triazole (0.72 g, 10.4 mmol) and methylformamide (6 mL). Cool in an ice bath and add sodium hydride (0.42 g, 60% i oil, 10.4 mmol). After 30 minutes, warm to ambient temperature. Add a solution of methyl 2-methoxy-5-chloromethylbenzoate (1.85 g, 6.74 mmol) in dimethylformamide (6 mL). Heat to 75° C. After 3 hours, partition the reaction mixture between water and ethyl acetate. Extract the organic layer with water, dry over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 95/5 dichloromethane/methanol containing 0.5% concentrated aqueous ammonia to give methyl 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoate: Rf=0.1 (silica gel, 1/1 hexane/ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. temperatureHeat to 75° C
  3. waitAfter 3 hours
  4. custompartition the reaction mixture between water and ethyl acetate
  5. extractionExtract the organic layer with water
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-81b5f91bc6f5441583bcdef6f4fccec9
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

Loading…