O=O.[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:10][CH2:11][C:4]1=2.C(O)(=[O:20])C(C)C>O>[O:20]=[C:11]1[C:4]2[S:3][CH:7]=[CH:6][C:5]=2[CH:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:10]1Oxygen is passed into a mixture of N-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)acetamide (1.0 g; 5.13 m mole), cobaltous acetate (0.25 g; 1.4 m mole), cobaltous bromide tetrahydrate (0.32 g; 1.1 m mole), isobutyric acid (20 ml) and water (0.2 ml) in a sintered glass funnel fitted with a condenser and thermometer, via the stem of the funnel. The dark brown mixture is oxygenated for 100 minutes at room temperature, then heated briefly to 48° C. After 2 hours and 10 minutes, the mixture is reheated to 50° C. and the flow of oxygen is terminated 2 hours later. The mixture is then worked up as described in Example 1 to attain a 37% yield of the title compound.
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