Dimethyl Sulfoxide → 2-Chloro-4-nitro-3-phenoxy-1-(4-cyano-phenoxy)-benzene

HRID 1902589Notes

Reaction equation

HRID 1902589 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)#[N:20].CS(C)=O.[OH-].[Na+]>O>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 131025432,3-Dichloro-6-nitro-1-phenoxy-benzene

Product 1

HCID 128811532-Chloro-4-nitro-3-phenoxy-1-(4-cyano-phenoxy)-benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14.2 gm of 2,3-dichloro-6-nitro-1-phenoxy-benzene, 6.5 gm of 4-cyano-phenol, 40 ml of dimethylsulfoxide and 50 ml of 10 N sodium hydroxide was stirred for 3 hours at 100° C. Thereafter, the reaction mixture was diluted with water, the aqueous mixture was extracted with chloroform, the organic extract solution was dried, and the chloroform was distilled off. The residue was purified by passing it through a silicagel column and recrystallizing it from ethanol, yielding 11 gm (60.2% of theory) of the colorless crystalline title compound, m.p. 140°-142° C.

Workup

  1. extractionthe aqueous mixture was extracted with chloroform
  2. customthe organic extract solution was dried
  3. distillationthe chloroform was distilled off
  4. customThe residue was purified
  5. customrecrystallizing it from ethanol

Sources & evidence

ORD record
ord-4e759ef5859b4e039bae80c18cfe1360
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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