Hydrochloric Acid → 3-[[3-[(3-Amino-1-methyl-1H-1,2,4-triazol-5-yl)amino]propyl]-amino]-N,N-dimethylbenzamide

HRID 325701Notes

Reaction equation

HRID 325701 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([N:11]([CH3:13])[CH3:12])=[O:10].[C:17]([N:19]=[C:20]([N:23]([CH3:32])[N:24]=CC1C=CC=CC=1)SC)#[N:18].Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:18][C:17]1[N:19]=[C:20]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([N:11]([CH3:12])[CH3:13])=[O:10])[N:23]([CH3:32])[N:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 212975663-[(3-Aminopropyl)amino]-N,N-dimethylbenzamideHCID 54323404methyl N-cyano-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate

Product 1

HCID 212975703-[[3-[(3-Amino-1-methyl-1H-1,2,4-triazol-5-yl)amino]propyl]-amino]-N,N-dimethylbenzamideYield 42.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[(3-Aminopropyl)amino]-N,N-dimethylbenzamide (0.8 g) and N-cyano-1-methyl-2-(phenylmethylene)hydrazine carboximidothioic acid, methyl ester (0.84 g) were heated together under reduced pressure of 14 mm Hg during 4 hr at 100°. The cooled reaction mixture was dissolved in acetone, treated with 1 N hydrochloric acid (2 ml) and heated at 60° for 0.5 hr. The mixture was cooled, basified with potassium carbonate and extracted with ethyl acetate. Evaporation of the organic extracts gave a viscous oil which was triturated with ether to give the title compound (0.49 g). TLC silica; methanol:ammonia (80:1) Rf 0.63. NMR (CDCl3) 2.9 m (1H); 3.2-3.7 m (3H); 5.28 t (1H); 6.12 s (2H); 6.7 s (3H); 7.0 s (6H); 6.4-7.4 m (5H); 8.23 t (2H).

Workup

  1. customThe cooled reaction mixture
  2. temperatureheated at 60° for 0.5 hr
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the organic extracts
  6. customgave a viscous oil which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-325fa511f1da4228a7d8b0a1dd80bdff
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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