Dichloromethane → HCID 178419703, compound

HRID 1262640Notes

Reaction equation

HRID 1262640 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1)(=O)[CH3:2].C(Cl)Cl.[Br:16]Br.[C:18]([NH:21][C:22]([NH2:24])=[S:23])(=[NH:20])[NH2:19]>CCOCC>[BrH:16].[C:11]([CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:1]2[N:24]=[C:22]([NH:21][C:18]([NH2:20])=[NH:19])[S:23][CH:2]=2)=[CH:5][CH:6]=1)#[N:12]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 24408BromineHCID 825054-AcetylphenylacetonitrileHCID 178513045HCID 178513045, compound

Product 1

HCID 178419703HCID 178419703, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 6.36 g. (0.04 mole) of p-acetylphenyl acetonitrile in 100 ml. of methylene chloride is added 6.40 g. (0.04 mole) of bromine in 50 ml. of methylene chloride. The reaction solution is warmed for a few minutes and the heat then removed. After a few minutes the bromine color disappears. The reaction mixture is stirred an additional 1/2 hour at room temperature. The methylene chloride is removed in vacuo on a rotary evaporator. To the residue is added 100 ml. of ethanol and 4.73 g. (0.04 mole) of amidinothiourea. The reaction mixture is heated with stirring for 1 hour under reflux, cooled in ice and then filtered. There is obtained 7.6 g. of product, m.p. 242°-246° (dec.). Recrystallization is from ethanol to which is then added enough water to form a solution. Ether is added to the cloudy point. There is obtained 5.9 g. of crystals, m.p. 259°-261° (dec.).

Workup

  1. temperatureThe reaction solution is warmed for a few minutes
  2. temperaturethe heat
  3. customthen removed
  4. waitAfter a few minutes the bromine color disappears
  5. customThe methylene chloride is removed in vacuo on a rotary evaporator
  6. additionTo the residue is added 100 ml
  7. temperatureThe reaction mixture is heated
  8. stirringwith stirring for 1 hour
  9. temperatureunder reflux
  10. temperaturecooled in ice
  11. filtrationfiltered
  12. customThere is obtained 7.6 g
  13. customRecrystallization
  14. additionis then added enough water
  15. customto form a solution
  16. customThere is obtained 5.9 g

Sources & evidence

ORD record
ord-42af59062f0b4aa9a09a4f18d914a98e
Source dataset
uspto-grants-1984_06
Patent number
US04452985

Reaction notes

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