Carbon Dioxide → 1-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-yl)urea

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Reaction Steps

A mixture of 4,5,6,7-tetrahydro-7-hydroxybenzo[b]-thien-4-yl urea (4 g., 18.87 mmole), sodium hydroxide (0.969 g., 24.22 mmole), paraformaldehyde (1.038 g., 34.6 mmole) and methanol (94 ml.) is stirred and heated at reflux under a nitrogen atmosphere for 23 hours. The mixture is allowed to cool and excess solid carbon dioxide is added. Evaporation in vacuo affords a solid which is stirred with water (50 ml.) for 2 hours, filtered and air dried to furnish 3.16 g., of the title compound (65% yield) m.p. 157°-159° C. dec. Recrystallization from hot acetone gives the analytical specimen 160°-161° C. dec.

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