Water → 5-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

HRID 324375

Reaction equation

HRID 324375 reaction equation
[CH3:1][S:2][C:3](=[C:6]([C:10]#[N:11])[C:7]([NH2:9])=[O:8])SC.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[NH:21][NH2:22].O>CO>[NH2:11][C:10]1[N:21]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([Cl:19])=[CH:16][C:15]=2[Cl:20])[N:22]=[C:3]([S:2][CH3:1])[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 113025915-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of bis(methythio)methylenecyanoacetamide (7.800 g, 50 mmol) and 2,4,6-trichlorophenylhydrazine (10.575 g, 50 mmol) in 250 ml of methanol was heated at reflux for 2.5 hours. The mixture was cooled and water was added. Precipitate formed and filtered to give 14.323 g (81.5% yield) of the title compound as a white solid. 1H NMR(CDCl3): 2.6 (s,3H), 5.5(brs, 2H), 7.5(s,2H) ppm. Recrystallization of a small portion of the solid from chloroform gave white crystals; m. p. 198-199° C. Anal. Calc. for C11H9Cl3N4OS: C, 37.57; H, 2.58; N, 15.93; Found: C, 37.54; H, 2.51; N, 15.73.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe mixture was cooled
  4. customPrecipitate formed
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c13c5fd8e8314a288ea8f87bcf3cb292
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Linked notes

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