3,4-Dichlorophenol → 2-(3,4-Dichlorophenoxy)-5-ethylthio-4-pyridinecarbonitrile

HRID 637795Notes

Reaction equation

HRID 637795 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH2:11][CH3:12])=[CH:4][N:3]=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[CH:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH2:11][CH3:12])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 135602112-Chloro-5-ethylthio-4-pyridinecarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 135602262-(3,4-Dichlorophenoxy)-5-ethylthio-4-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-5-ethylthio-4-pyridinecarbonitrile (4.0 g) was reacted with 3.6 g of 3,4-dichlorophenol in the presence of 2.6 g of t-BuOK in 40 ml of THF and 4 ml of DMSO. 5.5 g (84.6%) of the desired, 2-(3,4-dichlorophenoxy)-5-ethylthio-4-pyridinecarbonitrile was recovered, m.p. 68°-69° C.

Workup

  1. custom2-(3,4-dichlorophenoxy)-5-ethylthio-4-pyridinecarbonitrile was recovered

Sources & evidence

ORD record
ord-707a4ffc5d454e00833d5210d618aff8
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Reaction notes

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