Bromine → HCID 178419701, compound

HRID 1262639Notes

Reaction equation

HRID 1262639 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=O)[CH3:2].[Br:12]Br.[C:14]([NH:17][C:18]([NH2:20])=[S:19])(=[NH:16])[NH2:15]>C(Cl)Cl>[BrH:12].[C:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]2[N:20]=[C:18]([NH:17][C:14]([NH2:16])=[NH:15])[S:19][CH:2]=2)=[CH:5][CH:6]=1)#[N:9]

Participants

5

Reactant 3

HCID 24408BromineHCID 740444'-CyanoacetophenoneHCID 178513045HCID 178513045, compound

Product 1

HCID 178419701HCID 178419701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.5 g. (0.1 mole) of p-acetylbenzonitrile in 250 ml. of methylene chloride is added 16.0 g. (0.1 mole) of bromine. After a few minutes of stirring at room temperature, the solution turns colorless. Stirring is continued an additional 15 minutes. The methylene chloride is removed on a rotary evaporator and 350 ml. of ethanol is added to the residue. To the suspension is added 11.8 g. (0.1 mole) of amidinothiourea. The reaction mixture is heated under reflux for 1 hour, then cooled in ice. The precipitate which forms amounts to 26.9 g. Recrystallization from DMF-EtOH gives 22.4 g. of product with m.p. 293°-295°.

Workup

  1. stirringStirring
  2. customThe methylene chloride is removed on a rotary evaporator and 350 ml
  3. additionof ethanol is added to the residue
  4. additionTo the suspension is added 11.8 g
  5. temperatureThe reaction mixture is heated
  6. temperatureunder reflux for 1 hour
  7. temperaturecooled in ice
  8. customRecrystallization from DMF-EtOH
  9. customgives 22.4 g

Sources & evidence

ORD record
ord-14411bb375c6485bb6299e798ce323f2
Source dataset
uspto-grants-1984_06
Patent number
US04452985

Reaction notes

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