Toluene → HCID 178527702, compound

HRID 1532943Notes

Reaction equation

HRID 1532943 reaction equation
[Pt+2:1].Cl[C:3]1[C:4](=O)[C:5]([C:13]#[N:14])=[C:6]([C:11]#N)[C:7](=O)[C:8]=1Cl.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO.C(Cl)(Cl)Cl>[C:16]1([C:22]2[C:13]3[C:5]4[CH:4]=[CH:3][CH:8]=[CH:7][C:6]=4[C:11]([N:14]=3)=[C:13]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=3)[C:11]3[NH:14][C:13]([C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:11]4[N:14]=[C:13]([C:22]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[C:11]5[NH:14][C:13]=2[C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]5=2)[C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]4=2)=[C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]=32)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Pt+:1]

Participants

6

Reactant 3

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 105166Platinum(2+)

Product 1

HCID 178527702HCID 178527702, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

2.0 g (2 mmol) of platinum(II) tetraphenylcyclohexenoporphyrin according to Example B2 are mixed with 4.5 g (20 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 400 ml of toluene, and the mixture is heated at reflux for one hour. After cooling, the reaction mixture is taken up in methanol and filtered. There are obtained 1.8 g of crude product, which is dissolved in chloroform and then subjected to flash chromatography on silica gel. The green eluates are combined and the chloroform is removed in vacuo at 60° C. 1.4 g (71%) of a microcrystalline green powder are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for one hour
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customThere are obtained 1.8 g of crude product, which
  6. customthe chloroform is removed in vacuo at 60° C

Sources & evidence

ORD record
ord-09460ca367d64c1f9e6ba10fbf3f439b
Source dataset
uspto-grants-2001_03
Patent number
US06207461B1

Reaction notes

Loading…