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

HRID 637796Notes

Reaction equation

HRID 637796 reaction equation
Cl[C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]([S:8][CH2:9][CH3:10])=[N: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])=[CH:4][C:5]([S:8][CH2:9][CH3:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 135602125-Chloro-2-ethylthio-4-pyridinecarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 135602275-(3,4-Dichlorophenoxy)-2-ethylthio-4-pyridinecarbonitrileYield 36.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-2-ethylthio-4-pyridinecarbonitrile (5.4 g) was mixed with 5.4 g of 3,4-dichlorophenol in the presence of 3.7 g of t-BuOK in 30 ml of THF and 30 ml of DMSO. The mixture was heated at boiling temperature for about 70 hours to give 3.2 g (36%) of the desired 5-(3,4-dichlorophenoxy)-2-ethylthio-4-pyridinecarbonitrile, m.p. 79°-81° C.

Workup

  1. temperatureThe mixture was heated
  2. customfor about 70 hours

Sources & evidence

ORD record
ord-09bf00717649461e9d9fb96b8343f6d1
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Reaction notes

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