Phenol → HCID 13936027, compound

HRID 2292039Notes

Reaction equation

HRID 2292039 reaction equation
ClC1C=C(C=CC=1)C(O[CH:8]1[C:13](=[O:14])[NH:12][C:11]([CH3:15])=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[S:9]1)=O.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[OH:31][C:25]1[CH:30]=[CH:29][C:28]([CH:8]2[C:13](=[O:14])[NH:12][C:11]([CH3:15])=[C:10]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[S:9]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 139360302-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one

Product 1

HCID 13936027HCID 13936027, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Silica gel (Wakogel C-200, 40 mg) was added as catalyst to a solution of 2-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (0.98 g) and phenol (0.51 g) in acetonitrile (20 ml) and the mixture was stirred at 50° C. for 35 hours. The mixture was chromatographed on silica gel (Wakogel C-200) column, using chloroform-acetonitrile (=5:1) as an eluant. The residue was recrystallized from ethanol to give the titled compound (0.19 g, yield 23.4%) as pale yellow powder.

Workup

  1. customThe mixture was chromatographed on silica gel (Wakogel C-200) column
  2. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6b8a548a759c4f07a61b2fd461672d2c
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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