3,5-Diamino-1,2,4-triazole → HCID 136133146, compound

HRID 2200920Notes

Reaction equation

HRID 2200920 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[C:8]([C:14](=O)[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH:19]1[C:23]([NH2:24])=[N:22][C:21]([NH2:25])=[N:20]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:24][C:23]1[N:22]=[C:21]2[NH:25][C:14]([CH3:15])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]([C:6]3[CH:17]=[CH:18][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[N:20]2[N:19]=1

Participants

5

Reactant 3

HCID 150783,5-Diamino-1,2,4-triazoleHCID 367509HCID 367509, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 136133146HCID 136133146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
63 °C

Procedure

Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (12.2 g, 50.1 mmol; preparation see WO 2004/020410-A2, Example 32A) and 1H-1,2,4-triazole-3,5-diamine (6.0 g, 60.5 mmol, 1.2 eq.) were dissolved in DMF (150 ml). Solid sodium bicarbonate (30.7 g, 365.6 mmol, 6 eq.) was added, and the mixture was stirred at 63° C. for 12 h. The mixture was then filtered and the DMF was distilled off from the filtrate under reduced pressure. The residue was suspended in ethanol and stirred, and the product was then filtered off and dried under high vacuum. This gave 12.45 g (76% of theory) of the title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. distillationthe DMF was distilled off from the filtrate under reduced pressure
  3. stirringstirred
  4. filtrationthe product was then filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-cb0718a77edc4768b37a5dbc5577cee2
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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