m-ethylphenyl-N-methylcyanamide → Guanidine

HRID 1858982Notes

Reaction equation

HRID 1858982 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[ClH:13].[Br:14][C:15]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:16]=1[NH2:17]>ClC1C=CC=CC=1>[NH2:9][C:10]([NH2:11])=[NH:17].[ClH:13].[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]([NH:17][C:16]2[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:15]=2[Br:14])=[NH:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10103434m-ethylphenyl-N-methylcyanamideHCID 22120069HCID 22120069, compound

Product 2

HCID 3520GuanidineHCID 178436381HCID 178436381, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of N-(3-ethylphenyl)-N-methylcyanamide (520 mg, 3.3 mmol), 2,5-dibromoaniline hydrochloride (861 mg, 3 mmol), and chlorobenzene (2 mL) were combined in a dry round bottom flask equipped with water cooled condenser under nitrogen and placed in a preheated oil bath (150-160° C.). The reaction mixture was heated for 3 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-methyl-N'-(2,5-dibromophenyl)guanidine hydrochloride, as a white solid (780 mg, 59% yield).

Workup

  1. customwere combined in a dry round bottom flask
  2. customequipped with water cooled condenser under nitrogen
  3. customplaced in a preheated oil bath
  4. custom(150-160° C.)
  5. temperatureThe reaction mixture was heated for 3 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-e9ec4915c5b74eda8a7f1706dadc6151
Source dataset
uspto-grants-2000_11
Patent number
US06153604

Reaction notes

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