Dimethyl Sulfoxide → Tetracene-2,3-dicarbonitrile

HRID 703257

Reaction equation

HRID 703257 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[C:3]([CH:15]=O)[C:2]=1[CH:17]=O.[CH2:19]([C:23]#[N:24])[CH2:20][C:21]#[N:22].C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[C:21]([C:20]1[C:19]([C:23]#[N:24])=[CH:15][C:3]2[C:2](=[CH:1][C:14]3[C:5]([CH:4]=2)=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=3)[CH:17]=1)#[N:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8062SuccinonitrileHCID 11430Potassium CarbonateHCID 1959062,3-Anthracenedicarboxaldehyde

Product 1

HCID 22151701Tetracene-2,3-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 3.5 g of anthracene-2,3-dialdehyde (E. Mallonli et al., Synthesis 1980, page 689), 1.8 g of succinodinitrile, 3 g of K2CO3 and 250 ml of dimethyl sulfoxide is heated with stirring at 60°-70° C. for 30 minutes. It is then cooled to 15° C. and 50 ml of water are added. The precipitate which has been deposited is filtered off and is sublimed at 300° C. Yield 485 mg (12%), λmax : 772 nm.

Workup

  1. temperatureis heated
  2. filtrationThe precipitate which has been deposited is filtered off
  3. customis sublimed at 300° C

Sources & evidence

ORD record
ord-ee526a0c04e0434f81097a5df64a1cf1
Source dataset
uspto-grants-1991_01
Patent number
US04981962

Linked notes

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