Sodium → 2-Benzylthio-5,6-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 477221

Reaction equation

HRID 477221 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.[Na].[CH3:16][CH:17]([C:20](=O)[CH3:21])[CH:18]=O>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[C:20]([CH3:21])[C:17]([CH3:18])=[CH:16][N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 11051586Butanal, 2-methyl-3-oxo-HCID 178509291HCID 178509291, compound

Product 1

HCID 141550922-Benzylthio-5,6-dimethyl-1,2,4-triazolo[1,5-a]pyrimidineYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5.0 g (24 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 5.0 g (41 mmol) of the sodium salt of 2-methyl-3-oxobutanal in 200 ml of glacial acetic acid was heated at reflux overnight. The solution was cooled to room temperature and the reaction mixture was concentrated by evaporation at reduced pressure. The residue was combined with ice and H2O to separate a tan solid. The solid was collected by filtration, dried and carefully recrystallized from ethyl acetate to yield 3.53 g (54%) of the desired product as a crystalline solid, m.p. 147°-149° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux overnight
  2. concentrationthe reaction mixture was concentrated by evaporation at reduced pressure
  3. customto separate a tan solid
  4. filtrationThe solid was collected by filtration
  5. customdried
  6. customcarefully recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d3cc2949956845dba26dd21283252a72
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Linked notes

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