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

HRID 2230610Notes

Reaction equation

HRID 2230610 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-1eb44a0ca3674fc68135739be126b7a0
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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