Ammonium Hydroxide → 1-(3-Methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide

HRID 2412366Notes

Reaction equation

HRID 2412366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10]2[C:14](=O)[O:13][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[NH4+:23].[K+].[Br-]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][C:10]([C:14]([NH2:23])=[O:13])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 253877Potassium BromideHCID 178425636HCID 178425636, compound

Product 1

HCID 131321361-(3-Methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Three grams (0.01 mole) of 4-(3-methylphenyl-hydrazono)-2-phenyl-oxazoline-5-one (R1 =3--CH3, R2 =R3 =H in the formula II) was suspended in 93 ml of methanol. To the resulting suspension, 66.2 ml of 29% solution of ammonium hydroxide (0.549 mole) was added and refluxed for 5 minutes. Methanol and ammonia were then distilled off under a reduced pressure, and the resulting crystals were filtered out and washed with water. The crystals were recrystallized from a mixed solvent of 5.8 ml of methanol and 4.5 ml of water to obtain 1.8 g of almost colorless crystal, m.p. 142°-143° C., with a yield of 63%. I.R. (KBr, cm-1, refer to FIG. 2); 3500-3240 (broad and strong), 1700, 1670, 1610, 1458, 1400, 1302, 789 and 700.

Workup

  1. temperaturerefluxed for 5 minutes
  2. distillationMethanol and ammonia were then distilled off under a reduced pressure
  3. filtrationthe resulting crystals were filtered out
  4. washwashed with water
  5. customThe crystals were recrystallized from a mixed solvent of 5.8 ml of methanol and 4.5 ml of water
  6. customto obtain 1.8 g of almost colorless crystal, m.p. 142°-143° C.

Sources & evidence

ORD record
ord-5fec88f282a64ae5bf141b2f545a4cc0
Source dataset
uspto-grants-1985_01
Patent number
US04492597

Reaction notes

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