Ethanol → 2,6-diethyl-N-[(1-methyl-2-thiono-1,3,4-triazol-5-yl)-methyl]-aniline

HRID 1106214Notes

Reaction equation

HRID 1106214 reaction equation
C[NH:2][NH:3][C:4]([NH:6][C:7](=O)[CH2:8][NH:9][C:10]1[C:15]([CH2:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:18][CH3:19])=[S:5].[OH-].[K+].[CH2:23](O)C>O>[CH2:16]([C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:18][CH3:19])[C:10]=1[NH:9][CH2:8][C:7]1[N:6]([CH3:23])[C:4](=[S:5])[NH:3][N:2]=1)[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20232766HCID 20232766, compound

Product 1

HCID 130142452,6-diethyl-N-[(1-methyl-2-thiono-1,3,4-triazol-5-yl)-methyl]-anilineYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

29.6 g (0.1 mole) of 1-methyl-4-[(2,6-diethylanilino)-acetyl]-thiosemicarbazide were suspended in 150 ml of ethanol and, after added 7 g of potassium hydroxide in 20 ml of water, the mixture was heated under reflux for 1 hour. Thereafter, most of the solvent was distilled off and 250 ml of water were added to the residue. After acidifying the mixture to pH 5 with glacial acetic acid, the precipitate which formed was filtered off and washed thoroughly with water. After drying, 27 g (97% of theory) of 2,6-diethyl-N-[(1-methyl-2-thiono-1,3,4-triazol-5-yl)-methyl]-aniline of melting point 117° to 121° C. were obtained. ##STR83##

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationThereafter, most of the solvent was distilled off
  4. addition250 ml of water were added to the residue
  5. customthe precipitate which formed
  6. filtrationwas filtered off
  7. washwashed thoroughly with water
  8. customAfter drying

Sources & evidence

ORD record
ord-074e2ce771f444ac81cf588a9521f471
Source dataset
uspto-grants-1982_01
Patent number
US04312664

Reaction notes

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