Dimethyl Sulfoxide → 4,4'-[Naphthalene-2,7-diylbis(oxy)]di(benzene-1,2-dicarbonitrile)

HRID 1659604Notes

Reaction equation

HRID 1659604 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH:3]=1.[OH-].[Na+].CS(C)=O.[N+]([C:22]1[CH:23]=[C:24]([C:30]#[N:31])[C:25](=[CH:28][CH:29]=1)[C:26]#[N:27])([O-])=O>O.C1C=CC=CC=1>[C:26]([C:25]1[CH:28]=[C:29]([CH:22]=[CH:23][C:24]=1[C:30]#[N:31])[O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([C:30]#[N:31])[CH:23]=3)=[CH:7][CH:8]=2)[CH:3]=1)#[N:27]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 113972,7-NaphthalenediolHCID 14798Sodium HydroxideHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 197969784,4'-[Naphthalene-2,7-diylbis(oxy)]di(benzene-1,2-dicarbonitrile)Yield 59.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 4.0 g (0.025 mol) of 2,7-dihydroxynaphthalene (2.2 g, 0.054 mol) of 50% aqueous sodium hydroxide, 30 ml of dimethyl sulfoxide and 25 ml of benzene was heated at reflux under a nitrogen atmosphere for 4 hours. The water was azeotroped from the mixture with a Dean-Stark trap. The reaction content was cooled to room temperature and 8.7 g (0.05 mol) of 4-nitrophthalonitrile was added in one sum. The resulting mixture was stirred for 15 hours at room temperature and was then poured into 150 ml of water. The light-brown precipitate was collected by suction filtration, washed with water, dried at reduced pressure, and washed with hot absolute ethanol to yield 6.1 g (59%) of the desired product, m.p. 201°-204° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 4 hours
  3. customThe water was azeotroped from the mixture with a Dean-Stark trap
  4. filtrationThe light-brown precipitate was collected by suction filtration
  5. washwashed with water
  6. customdried at reduced pressure
  7. washwashed with hot absolute ethanol

Sources & evidence

ORD record
ord-87b63b1f31684d0c96bc64b46b9c519a
Source dataset
uspto-grants-1981_12
Patent number
US04304896

Reaction notes

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