Hydrogen Peroxide → HCID 1082733, compound

HRID 390781Notes

Reaction equation

HRID 390781 reaction equation
[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:27]([O:29]CC)=[O:28])=[C:9]([NH:12][C:13](=[O:26])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[S:10][CH:11]=2)=[CH:3][CH:2]=1.[Li+].[OH-].OO.[OH-].[Na+]>O>[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:27]([OH:29])=[O:28])=[C:9]([NH:12][C:13](=[O:26])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[S:10][CH:11]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium Hydroxide2×HCID 14798Sodium HydroxideHCID 1537197HCID 1537197, compound

Product 1

HCID 1082733HCID 1082733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ethyl cyanoacetate (5 mmol), and 1-(3,4,5-trimethoxyphenyl)ethanone (5 mmol) are dissolved in toluene (5 mL). Morpholine (5 mmol) is added followed by activated molecular sieves (4A). The reaction is stirred at 80° C. for 12 hours. The reaction is cooled to room temperature, filtered and concentrated. The residue is taken up in toluene (5 mL), ethanol (5 mL) and sulfur is added (0.16 g; 5 mmol). The reaction mixture is heated with mixing at 70° C. for 12 hours. The reaction is cooled to room temperature and the solvents are evaporated. The residue is purified by HPLC to provide ethyl 2-amino-4-(3,4,5-trimethoxyphenyl)thiophene-3-carboxylate. Ethyl 2-amino-4-(3,4,5-trimethoxyphenyl)thiophene-3-carboxylate (5 mmol) is treated with 4-methylbenzoyl chloride (5 mmol) in THF (10 mL). The reaction is stirred at room temperature for 10 hours. The reaction is diluted with 1N NaOH (10 mL) and ethyl acetate (15 mL). The layers are separated, the organic layer is dried with anhydrous sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography to provide ethyl 4-p-tolyl-2-(3,4,5-trimethoxybenzamido)thiophene-3-carboxylate. Ethyl 4-p-tolyl-2-(3,4,5-trimethoxybenzamido)thiophene-3-carboxylate is hydrolyzed under a variety of conditions (e.g. LiOH, water; LiOH, H2O2, water; or NaOH, water) to provide the title compound

Sources & evidence

ORD record
ord-cf8a2ed3b4194c9696c753b3031eda5a
Source dataset
uspto-grants-2013_02
Patent number
US08383670B2

Reaction notes

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