1-(2,4-Dihydroxy-3-methylphenyl)ethan-1-one → 6-(4-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) isonicotinonitrile

HRID 2267071Notes

Reaction equation

HRID 2267071 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[N:11]=[CH:12][CH:13]=[C:14]([CH:17]=2)[C:15]#[N:16])=[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[N:11]=[CH:12][CH:13]=[C:14]([CH:17]=3)[C:15]#[N:16])=[CH:7][CH:8]=2)=[C:24]([CH3:25])[C:19]=1[OH:18])(=[O:29])[CH3:28]

Participants

3

Reactant 2

HCID 5921391-(2,4-Dihydroxy-3-methylphenyl)ethan-1-oneHCID 685330586-(4-(Hydroxymethyl)phenylthio) isonicotinonitrile

Product 1

HCID 685358616-(4-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) isonicotinonitrileYield 69.4%

Procedure

Using the method of Preparation 166 using 6-(4-(hydroxymethyl)phenylthio) isonicotinonitrile (1.10 g, 4.54 mmol) and 1-(2,4-dihydroxy-3-methylphenyl)ethanone (754 mg, 4.54 mmol) affords the title compound (1.23 g, 69%). MS (APCI-neg) m/z (rel intensity): 389 (M−H, 100%).

Sources & evidence

ORD record
ord-e718691bf11b4baa9b1f1f02319ef0f8
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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