Benzylhydrazine dihydrochloride → HCID 10850983, compound

HRID 1602217Notes

Reaction equation

HRID 1602217 reaction equation
C[O-].[Na+].Cl.Cl.[CH2:6]([NH:13][NH2:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15]([C:17](=[C:20](SC)[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]#[N:19])#[N:16]>CO.C(O)C>[NH2:19][C:18]1[N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:14]=[C:20]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:17]=1[C:15]#[N:16]

Participants

6

Reactant 3

HCID 146540Benzylhydrazine dihydrochlorideHCID 1704453HCID 1704453, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10850983HCID 10850983, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

With ice-cooling, 19.3 ml of a 5.4N sodium methanolate solution in 20 ml of methanol (purissimum) are added to 9.9 g of benzylhydrazine dihydrochloride in 20 ml of methanol (purissimum) and the reaction mixture is stirred for approx. 15 minutes at room temperature and then introduced into a solution of 4.65 g of 2-cyano-3-methylmercapto-3-phenylamino-acrylonitrile in 150 ml of absolute ethanol. The mixture is heated under reflux for approx. 17 hours and cooled to room temperature and insoluble material is filtered off with suction. The filtrate is concentrated by evaporation using a rotary evaporator and the brown oily residue is chromatographed on 190 g of silica gel, methylene chloride/ethyl acetate mixtures being used as eluant. 5-Amino-1-benzyl-4-cyano-3-phenylamino-pyrazole is obtained; m.p. 139-140° C., FAB-MS: (M+H)+ =290 (C17H15N5).

Workup

  1. temperatureWith ice-cooling
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for approx. 17 hours
  4. temperaturecooled to room temperature
  5. filtrationinsoluble material is filtered off with suction
  6. concentrationThe filtrate is concentrated by evaporation
  7. customa rotary evaporator
  8. customthe brown oily residue is chromatographed on 190 g of silica gel, methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-320d861e0100417b9c10b5c40b874f19
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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