3,4-Dichlorophenol → HCID 13560229, compound

HRID 637797Notes

Reaction equation

HRID 637797 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH3:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[CH:17][C:18]=1[Cl:19].CC([O-])(C)C.[K+]>C1COCC1.CS(C)=O>[Cl:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:20][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 13560203HCID 13560203, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13560229HCID 13560229, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-3-methylthio-2-pyridinecarbonitrile was mixed with 16.3 g of 3,4-dichlorophenol in the presence of 11.2 g of t-BuOK in 150 ml THF and 15 ml of DMSO. 13.4 g (54%) of the desired, 6-(3,4-dichlorophenoxy)-3-methylthio-2-pyridinecarbonitrile was recovered, m.p. 156°-158° C.

Workup

  1. custom6-(3,4-dichlorophenoxy)-3-methylthio-2-pyridinecarbonitrile was recovered

Sources & evidence

ORD record
ord-696e3e70c1a74939a3aa0c77c7d651b9
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Reaction notes

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