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1-(2,4-Dihydroxy-3-methylphenyl)ethan-1-one → 5-(4-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) picolinonitrile

HRID 2267065
Notes
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Reaction equation

HRID 2267065 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=2)=[CH:5][CH:4]=1.[OH:18][C:19]1[C:24]([CH3:25])=[C:23](O)[CH:22]=[CH:21][C:20]=1[C:27](=[O:29])[CH3:28]>>[C:27]([C:20]1[CH:21]=[CH:22][C:23]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([S:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=3)=[CH:7][CH:8]=2)=[C:24]([CH3:25])[C:19]=1[OH:18])(=[O:29])[CH3:28]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 5921391-(2,4-Dihydroxy-3-methylphenyl)ethan-1-oneHCID 685392925-(4-(Hydroxymethyl)phenylthio)picolinonitrile

Product 1

HCID 685358755-(4-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) picolinonitrileYield 65%

Procedure

Using the method of Preparation 166 using 5-(4-(hydroxymethyl)phenylthio) picolinonitrile (1.90 g, 7.84 mmol) and 1-(2,4-dihydroxy-3-methylphenyl)ethanone (1.30 g, 7.84 mmol) affords the title compound (1.98 g, 65%). MS (APCI-neg) m/z (rel intensity): 389 (M−H, 100%).

Sources & evidence

ORD record
ord-b9a6f69c423c4de587bdd480d4443d0a
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858646B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes