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

HRID 464560Notes

Reaction equation

HRID 464560 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 mol) of 1-methyl-4-[(2,6-diethylanilino)-acetyl]-thiosemicarbazide were suspended in 150 ml of ethanol and, after adding 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 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. ##STR88##

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 formed
  6. filtrationwas filtered off
  7. washwashed thoroughly with water
  8. customAfter drying

Sources & evidence

ORD record
ord-144ec86003a24862a01f5fdc02f5f6f0
Source dataset
uspto-grants-1985_10
Patent number
US04548639

Reaction notes

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