Methanethiol → 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile

HRID 1068873Notes

Reaction equation

HRID 1068873 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([NH:11][C:12](SC)=[C:13]([C:16]#[N:17])[C:14]#[N:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CS>CO>[NH2:15][C:14]1[NH:3][N:2]=[C:12]([NH:11][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:13]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 24654Hydrazine hydrate (1:1)HCID 1704435Propanedinitrile, [(methylthio)[(phenylmethyl)amino]methylene]-

Product 1

HCID 108224725-amino-3-benzylamino-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

24 ml (0.48 mol) of hydrazine hydrate are added dropwise to a solution of 92 g (0.4 mol) of 3-benzylamino-3-methylsulfanyl-2-cyano-acrylonitrile in 400 ml of methanol, the temperature rising to 40° C. The reaction mixture is slowly heated to boiling (e evolution of MeSH!), boiled for 2 hours, cooled to RT and concentrated by evaporation to a residual volume of ≈200 ml. Dilution with diethyl ether, filtration and washing with diethyl ether yield 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile [Spectrochimica Acta, 47A, 1635 (1991)]; m.p. 150-152° C.; TLC: Rf=0.41 (ethyl acetate).

Workup

  1. customrising to 40° C
  2. temperatureThe reaction mixture is slowly heated
  3. concentrationconcentrated by evaporation to a residual volume of ≈200 ml
  4. filtrationDilution with diethyl ether, filtration
  5. washwashing with diethyl ether

Sources & evidence

ORD record
ord-cb80dfdd3e074f0f89f6afabafb39d70
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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