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

HRID 1155640

Reaction equation

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]1

Participants

Conditions

Temperature: 48 °C

Procedure

Oxygen 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.

Workup

customfitted with a condenser
customThe dark brown mixture is oxygenated for 100 minutes at room temperature
custom10 minutes
customis reheated to 50° C.
customthe flow of oxygen is terminated 2 hours later

Sources & evidence

ORD record: ord-bcc2d5ee189e42939b6ab27fa5748507
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04332724

Linked notes

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