Acetone → Acetamide, N-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)-

HRID 127021Notes

Reaction equation

[CH3:1][C:2]([CH3:4])=[O:3].[S:5]1[CH:9]=[CH:8][C:7]2[CH:10]([NH:14][C:15](=[O:17])[CH3:16])[CH2:11]CCC1=2.S([O-])([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(C)C>[O:3]=[C:2]1[C:4]2[S:5][CH:9]=[CH:8][C:7]=2[CH:10]([NH:14][C:15](=[O:17])[CH3:16])[CH2:11][CH2:1]1

Participants

Conditions

Temperature: 10 °C

Procedure

Acetone (200 ml), N-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl) acetamide (9.75 g, 0.05 mol) and magnesium sulfate (21.0 g, 0.17 mol) are mixed, stirred and cooled to 10° C. Next, 150 ml of an aqueous potassium permanganate solution (prepared from 21.0 g, 0.133 mol of potassium permanganate and 200 ml of water) is added over 15 minutes to the above mixture, and the whole stirred for 3 hours. After 3 hours reaction time, analysis of the mixture by high pressure liquid chromatography (HPLC) indicates the reaction to be incomplete. The remainder of the above potassium permanganate solution (~50 ml) is added and the reaction mixture stirred for two more hours. Isopropanol (20 ml) is then added, the reaction mixture stirred overnight, and filtered. HPLC analysis of the filtered solution indicates a 73.6% yield of title product, and also the presence of 2% of starting material.

Workup

stirringthe whole stirred for 3 hours
customAfter 3 hours reaction time, analysis of the mixture by high pressure liquid chromatography (HPLC)
customthe reaction
stirringthe reaction mixture stirred for two more hours
stirringthe reaction mixture stirred overnight
filtrationfiltered

Sources & evidence

ORD record: ord-2393d935f34849278ec1060f71ea4d4e
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254268

Reaction notes

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