Methanol → HCID 15007244, compound

HRID 345096Notes

Reaction equation

HRID 345096 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[K+].Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19]>C(OCC)(=O)C>[C:1]1([C:7]2[N:11]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:10]=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 7295Methyl chloroacetateHCID 14797Potassium HydroxideHCID 178418369HCID 178418369, compound

Product 1

HCID 15007244HCID 15007244, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Two grams of 5-phenyltetrazole (13.68 mM) were slowly added to 5 ml of a methanol solution containing 770 mg (13.68 mM) of potassium hydroxide at room temperature. Two milli liters of a methanol solution containing 1.48 g (13.68 mM) of methyl chloroacetate were dropwise added to the resultant solution at room temperature. After the completion of the addition, the reaction solution was refluxed for 20 hours and cooled. The reaction solution was diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (elute is chloroform), to give 0.54 g of methyl 5-phenyl-1-tetrazoleacetate (yield: 18.1%).

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe reaction solution was refluxed for 20 hours
  3. temperaturecooled
  4. washwashed with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elute is chloroform)

Sources & evidence

ORD record
ord-bb1d73db3aac4e8d90f1769d9ad4ca56
Source dataset
uspto-grants-1991_10
Patent number
US05055481

Reaction notes

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