3,5-Dichloroaniline → 1-Cyano-3-(3,5-dichlorophenyl)guanidine

HRID 2166307Notes

Reaction equation

HRID 2166307 reaction equation
[N-:1]([C:4]#[N:5])[C:2]#[N:3].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[NH2:11]>Cl.O>[C:2]([NH:1][C:4]([NH:11][C:10]1[CH:9]=[C:8]([Cl:7])[CH:14]=[C:13]([Cl:15])[CH:12]=1)=[NH:5])#[N:3]

Participants

5

Reactant 2

HCID 122813,5-DichloroanilineHCID 4350929Sodium dicyanamide

Product 1

HCID 1785123601-Cyano-3-(3,5-dichlorophenyl)guanidineYield 76.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4.45 g (0.05 mol) of sodium dicyanamide in 50 ml of 1N HCl is added 8.1 g (0.05 mol) of 3,5-dichloroaniline in 50 ml of H2O. The mixture is heated to about 80° C. to 100° C. for two hours. The mixture is then cooled, and the precipitated solids are recovered by filtration, washed and dried to give 8.75 g of the desired product having a melting point of 196° C. -198° C.

Workup

  1. temperatureThe mixture is heated to about 80° C. to 100° C. for two hours
  2. temperatureThe mixture is then cooled
  3. filtrationthe precipitated solids are recovered by filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-4f2c080e88e94860bf173d81c7490c0f
Source dataset
uspto-grants-1990_07
Patent number
US04944788

Reaction notes

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