HCID 86742907, compound → HCID 14155083, compound

HRID 619921Notes

Reaction equation

HRID 619921 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.[CH2:15]([CH:17](CC)C(O)=O)[CH3:16].C(C(CC)C(O)=O)C.C(=O)CC=O>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[CH:16][CH:15]=[CH:17][N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 86742907HCID 86742907, compoundHCID 178509291HCID 178509291, compound

Product 1

HCID 14155083HCID 14155083, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.0 g (9.6 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 2.3 ml (9.6 mmol) of malonaldehyde bis(diethylacetate) in 20 ml of glacial acetic acid was heated at reflux for 17 hours. After cooling to room temperature, the solvent was removed by evaporation at reduced pressure. The brown solid residue was recrystallized from isopropyl alcohol to afford 0.4 g (17%) of the desired product as a light brown crystalline solid, m.p. 104°-106° C. IR and 1H NMR spectra were consistent with the assigned structure.

Workup

  1. temperatureat reflux for 17 hours
  2. customthe solvent was removed by evaporation at reduced pressure
  3. customThe brown solid residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-05b0557644ed4b3784f05622d6757443
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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