3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → N-[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]-1-methyl-3-[(methylsulphonyl)methyl]-1H-1,2,4-triazol-5-amine

HRID 652100Notes

Reaction equation

HRID 652100 reaction equation
[CH3:1][N:2]([C:11](SC)=[N:12][C:13](=O)[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:3]=CC1C=CC=CC=1.[CH3:22][N:23]([CH2:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[O:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH3:24]>C1(C)C=CC=CC=1.Cl>[CH3:22][N:23]([CH2:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[O:29][CH2:30][CH2:31][CH2:32][NH:33][C:11]1[N:2]([CH3:1])[N:3]=[C:13]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:12]=1)[CH3:24]

Participants

5

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 70434558Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate

Product 1

HCID 20199178N-[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]-1-methyl-3-[(methylsulphonyl)methyl]-1H-1,2,4-triazol-5-amineYield 80.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate (1.3 g) and 3-[3-[(dimethylamino)methyl]phenoxy]propanamine (0.81 g) were heated at 70° under water vacuum for 1 h. After cooling, the reaction mixture was dissolved in toluene (10 ml) and 5N hydrochloric acid (6 ml), and stirred at 20° during 18 h. The acidic layer was washed with toluene and basified (pH 10) with potassium carbonate. The mixture was then extracted with ethyl acetate to give the title compound (1.2 g) as an oil. T.l.c. System A Rf 0.39.

Workup

  1. temperatureAfter cooling
  2. washThe acidic layer was washed with toluene and basified (pH 10) with potassium carbonate
  3. extractionThe mixture was then extracted with ethyl acetate

Sources & evidence

ORD record
ord-351f8cc057de4b9f89f8de4c77ba2da3
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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