Hydrochloric Acid → 5-benzyl-1H-1,2,4-triazol-3-amine

HRID 1289784Notes

Reaction equation

HRID 1289784 reaction equation
[C:1]1([CH2:7][C:8](OC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[C:13]([NH:16][NH2:17])([NH2:15])=[NH:14].Cl.Cl.C(=O)([O-])O.[Na+]>CO>[NH2:15][C:13]1[N:14]=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:17][N:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7559Methyl phenylacetateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 178418668HCID 178418668, compound

Product 1

HCID 11166975-benzyl-1H-1,2,4-triazol-3-amineYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The synthesis method of Example 7-(2) was applied. Methyl phenylacetate (10.0 g), methanol (160 ml), metallic sodium (5.73 g) and aminoguanidine hydrochloride (27.5 g) were used as reagents. After the reaction, the reaction mixture was poured into ice water and adjusted to pH 8 with 2N hydrochloric acid and sodium hydrogencarbonate. Methanol was distilled away under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure to give a white solid. The solid was washed with ethyl acetate to give 7.12 g of white crystals (yield 61%).

Workup

  1. customAfter the reaction
  2. distillationMethanol was distilled away under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customto give a white solid
  7. washThe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-6d530a5889474414baefdf38b2080d61
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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