Methanol → HCID 45496685, compound

HRID 1361023Notes

Reaction equation

HRID 1361023 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1.C(Cl)Cl.CO>[OH-].[Na+]>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 2991808methyl 4-(2H-tetrazol-5-ylmethoxy)benzoate

Product 1

HCID 45496685HCID 45496685, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-(2H-Tetrazol-5-ylmethoxy)-benzoate was refluxed in 3N sodium hydroxide. The reaction was followed by TLC (DCM:MeOH=9:1). The reaction mixture was cooled, acidified and the product filtered off. The impure product was washed with DCM, dissolved in MeOH, filtered and purified by column chromatography on silica gel (DCM:MeOH=9:1). The resulting product was recrystallised from DCM:MeOH=95:5. This was repeated until the product was pure. This afforded 13.82 g (30%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe product filtered off
  3. washThe impure product was washed with DCM
  4. dissolutiondissolved in MeOH
  5. filtrationfiltered
  6. custompurified by column chromatography on silica gel (DCM:MeOH=9:1)
  7. customThe resulting product was recrystallised from DCM

Sources & evidence

ORD record
ord-70cb706c47304725a09ec0cb20e915b6
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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