2,5-Dichlorophenylcyanamide → N-(3-ethylphenyl)-N'-(2,5-dichlorophenyl)guanidine mesylate

HRID 1274096Notes

Reaction equation

HRID 1274096 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10]#[N:11].[S:12]([OH:16])(=[O:15])(=[O:14])[CH3:13].[CH2:17]([C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])[CH3:18]>ClC1C=CC=CC=1>[S:12]([OH:16])(=[O:15])(=[O:14])[CH3:13].[CH2:17]([C:19]1[CH:20]=[C:21]([NH:22][C:10]([NH:9][C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])=[NH:11])[CH:23]=[CH:24][CH:25]=1)[CH3:18]

Participants

4

Reactant 2

HCID 107027292,5-DichlorophenylcyanamideHCID 867560113-Ethylaniline mesylate

Product 1

HCID 178436393N-(3-ethylphenyl)-N'-(2,5-dichlorophenyl)guanidine mesylate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2,5-dichlorophenylcyanamide (1.02 g, 5.5 mmol), 3-ethylaniline mesylate (1.1 g, 5 mmol), and chlorobenzene (15 mL) were combined in a dry round bottom flask equipped with a water cooled condenser under nitrogen and placed in a preheated oil bath (150-160° C.). The reaction mixture was heated for 2 hours. After cooling, the crude reaction product was purified by crystallization from chlorobenzene/diethylether. The resulting crystals were collected by filtration, washed with diethylether, and dried in a vacuum oven (40° C., 15 hours) to yield the title compound, N-(3-ethylphenyl)-N'-(2,5-dichlorophenyl)guanidine mesylate, as a white solid (1.5 g, 75% yield).

Workup

  1. customwere combined in a dry round bottom flask
  2. customequipped with a water cooled condenser under nitrogen
  3. customplaced in a preheated oil bath
  4. custom(150-160° C.)
  5. temperatureThe reaction mixture was heated for 2 hours
  6. temperatureAfter cooling
  7. customthe crude reaction product
  8. customwas purified by crystallization from chlorobenzene/diethylether
  9. filtrationThe resulting crystals were collected by filtration
  10. washwashed with diethylether
  11. customdried in a vacuum oven (40° C., 15 hours)

Sources & evidence

ORD record
ord-7499b5712b9740deabd88f377c1ff383
Source dataset
uspto-grants-2000_12
Patent number
US06156741

Reaction notes

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