3,4-Dichlorophenol → HCID 13560225, compound

HRID 637794Notes

Reaction equation

HRID 637794 reaction equation
Cl[C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([S:8][CH2:9][CH3:10])=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].CC([O-])(C)C.[K+]>C1COCC1.CS(C)=O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([S:8][CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 13560204HCID 13560204, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13560225HCID 13560225, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure substantially the same as that described in Example 20, 8.0 g of 3-chloro-6-ethylthio-2-pyridinecarbonitrile was reacted with 8.2 g of 3,4-dichlorophenol in the presence of 5.6 g of t-BuOK in 60 ml of THF and 30 ml of DMSO. The reaction was allowed to proceed at boiling temperature for about 40 hours. The product, an oil, was purified by distillation on a Kugelrohr distillation apparatus, separated on a Water's Prep LC 500 instrument, and again distilled on a Kugelrohr apparatus to give about 7 g (54%) of the desired 3-(3,4-dichlorophenoxy)-6-ethylthio-2-pyridinecarbonitrile, having a boiling point (b.p.) of 160° C. at 0.01 mm Hg pressure.

Workup

  1. customfor about 40 hours
  2. distillationThe product, an oil, was purified by distillation on a Kugelrohr distillation apparatus
  3. customseparated on a Water'
  4. distillationagain distilled on a Kugelrohr apparatus

Sources & evidence

ORD record
ord-e357cdff050549c98738fa1824272f4e
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Reaction notes

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