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4-Hydroxybenzophenone → 2-Pyridinecarbonitrile, 6-(4-benzoylphenoxy)-3-(ethylthio)-

HRID 637798
Notes
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Reaction equation

HRID 637798 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[C:13]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC([O-])(C)C.[K+]>C1COCC1.CS(C)=O>[C:13]([C:21]1[CH:22]=[CH:23][C:24]([O:27][C:2]2[N:7]=[C:6]([C:8]#[N:9])[C:5]([S:10][CH2:11][CH3:12])=[CH:4][CH:3]=2)=[CH:25][CH:26]=1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 143474-HydroxybenzophenoneHCID 13560201HCID 13560201, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 5119312-Pyridinecarbonitrile, 6-(4-benzoylphenoxy)-3-(ethylthio)-Yield 28.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

6-Chloro-3-ethylthio-2-pyridinecarbonitrile (23.8 g) was mixed with 25.8 g of 4-benzoylphenol in the presence of 15.7 g of t-BuOK in 150 ml of THF and 30 ml DMSO. After reaction, the mixture was filtered leaving a solid residue from which 12.4 g of the desired 6-(4-benzoylphenoxy)-3-ethylthio-2-pyridinecarbonitrile (m.p. 88°-90° C.) was recovered. An additional 6.5 g of desired product was isolated from the filtrate by separation on a Water's Prep LC 500 instrument (using a 10% acetone in hexane eluant).

Workup

  1. customAfter reaction
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-3c0ae4f943cc424f8709a9f6bca19846
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04558134

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes