m-ethylphenyl-N-methylcyanamide → HCID 178436381, compound

HRID 1274094Notes

Reaction equation

HRID 1274094 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>[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

4

Reactant 2

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

Product 1

HCID 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 chlorobenzeneldiethylether. 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 chlorobenzeneldiethylether
  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-48ec4458ac504ee4af07f68b90e8261c
Source dataset
uspto-grants-2000_12
Patent number
US06156741

Reaction notes

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