Catechol → HCID 19922197, compound

HRID 1488751Notes

Reaction equation

HRID 1488751 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=1[C:12]#[N:13])([O-])=O.[C:14]1([C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)O)[OH:15].[C:22](=[O:25])([O-])[O-].[K+].[K+].O>CS(C)=O>[C:12]([C:5]1[C:6]([C:7]#[N:8])=[CH:9][CH:10]=[CH:11][C:4]=1[O:15][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[O:25][C:22]1[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=1[C:12]#[N:13])#[N:13]

Participants

6

Reactant 4

HCID 289CatecholHCID 962WaterHCID 11430Potassium CarbonateHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

Product 1

HCID 19922197HCID 19922197, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The same apparatus as was used in Example 1 was also used in this example. 3 g (0.0173 moles) of 3-nitrophthalonitrile, was dissolved in 15 ml of anhydrous dimethyl sulphoxide in the three-necked flask. 0.95 g (0.00863 moles) of catechol and 2 g of potassium carbonate were added to the reaction mixture. The mixture was stirred at room temperature with a stream of dry, oxygen-free nitrogen passing through the flask for 26 hours. The product was isolated by pouring the reaction mixture into 300 ml of water. The resultant solid precipitate was filtered and washed until the effluent was neutral. The product (which was an off-white powder) was recrystallized from methanol/acetonitrile (20/80) to yield off-white crystals of 1,2-bis-(2,3-dicyanophenoxy) benzene having the formula: ##STR9## The melting point was 158°-159° C. The elemental analysis for C22H10N4O2 was calc.: C, 72.92%; H, 2.76%; N, 15.67%; found: C, 72.57%; H, 2.72%; N, 15.43%.

Workup

  1. customof dry
  2. customThe product was isolated
  3. filtrationThe resultant solid precipitate was filtered
  4. washwashed until the
  5. customwas recrystallized from methanol/acetonitrile (20/80)

Sources & evidence

ORD record
ord-387d0094ae044e15a808dc8564f99d65
Source dataset
uspto-grants-1997_10
Patent number
US05675020

Reaction notes

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