Sodium Bicarbonate → 1-(2-Methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 628495Notes

Reaction equation

HRID 628495 reaction equation
Br[CH2:2][C:3]1[C:8]([Br:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1.C[O-].[Na+].[C:20](=O)(O)[O-:21].[Na+]>O1CCCC1>[CH3:20][O:21][CH2:2][C:3]1[C:8]([Br:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 898756621-(2-Bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Product 1

HCID 898762251-(2-Methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one 45.0 g, sodium methoxide 37.4 g and tetrahydrofuran 600 ml was stirred at room temperature for three hours. To the reaction mixture was added aqueous saturated sodium bicarbonate solution and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution and was dried over anhydrous magnesium sulfate. The resulting mixture was concentrated under reduced pressure to give 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one 36.2 g.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium bicarbonate solution
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64e1bc762b704889896dddabedffa327
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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