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

HRID 323408Notes

Reaction equation

HRID 323408 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].CCCCCC.C(OCC)(=O)C>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:17]([CH2:20][N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 240622Methyl 5-(chloromethyl)-2-methoxybenzoateHCID 21226206Ethyl acetate hexaneHCID 178418441HCID 178418441, compound

Product 1

HCID 18465024methyl 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Combine tetrazole (0.45 g, 6.42 mmol) and dimethylformamide (6 mL). Cool in an ice bath and add sodium hydride (0.26 g, 60% i oil, 6.5 mmol). After 30 minutes, warm to ambient temperature. Add a solution of methyl 2-methoxy-5-chloromethylbenzoate (1.13 g, 4.12 mmol) in dimethylformamide (10 (mL). Heat to 75° C. After 5.5 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 7/3 hexane/ethyl acetate to give methyl 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoate: Rf=0.67 (silica gel, ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. temperatureHeat to 75° C
  3. waitAfter 5.5 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-56752fa456544f7f853fb2b81c58e024
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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