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AssigneeAmerican Cyanamid Company
InventorGoro Asato
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This invention relates to 1-benzoyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)urea, 1-benzoyl-3-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)urea, and derivatives thereof and a method for the preparation of said compounds and substituted derivatives. Both of the above referred-to compounds are novel and useful intermediates for the preparation of the corresponding tetrahydrobenzo[b]thien-4-ylurea and tetrahydro-7-oxobenzo[b]thien-4-ylurea, respectively. The latter compounds and certain derivatives thereof are animal growth promoting agents.
dl -1-Benzoyl-3-(4,5,6,7-tetrahydrobenzo-[b]-thien-4-yl)urea.
d-1-Benzoyl-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea.
1-1-Benzoyl-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea.
d1-1-Benzoyl-3-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)urea.
d- 1-Benzoyl-3-(4,5,6,7-tetrahydro-7-oxobenzo-[b]thien-4-yl)urea.
1-1-Benzoyl-3-(4,5,6,7-tetrahydro-7-oxobenzo-[b]thien-4-yl)urea.
Dependencies are inferred from the claim text.
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Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached…
Heterocyclic compounds: containing oxygen or sulfur as hetero atom
Heterocyclic compounds
Fodder
Term ended 11 Oct 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
This invention relates to novel compounds of the formula: ##STR1## wherein X is selected from hydrogen, methyl, methoxy, chloro and nitro; Z is selected from hydrogen, chloro and nitro; Y is selected from ##STR2## and said compounds may be the racemic mixtures or the optically active isomers thereof.
This invention also relates to methods for the preparation of the above-identified formula (I) compounds, which may be the racemic mixtures or the optically active isomers thereof.
In accordance with this invention, a formula (I) compound, wherein Y is selected from ##STR3## can be prepared by reacting the corresponding thiophen-4-amine of formula (II), or an acid addition salt thereof, with benzoyl (or a substituted benzoyl) isocyanate as hereinbelow graphically illustrated: ##STR4## wherein X is selected from hydrogen, methyl, methoxy, chloro and nitro; Z is selected from hydrogen, chloro and nitro; Y is selected from ##STR5## HA represents an acid selected from hydrochloric, hydrobromic and hydriodic acid; n is 0 or 1; and said formulae (I) and (II) compounds are the racemic mixtures or the optical isomers thereof.
A solution of benzoyl isocyanate (2.94g) in methylene chloride (5ml) is added to a solution of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine is methylene chloride (50ml) under a nitrogen atmosphere. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness in vacuo. The residue is then stirred in ether (100ml) and filtered to afford 1-benzoyl-3-(4,5,6,7-tetrahydrobenzo-[b]thien-4-yl)urea, m.p. 189.degree. to 194.degree. C.
In the same manner, (+)-4,5,6,7-tetrahydrobenzo-[b]thiophen-4-amine is used in place of dl -4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine to afford the optically active title compound.
Similarly, substituted (X,Z)-benzoyl isocyanates are used in place of benzoyl isocyanate to afford the corresponding 1-(substituted benzoyl)-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl) ureas as follows: ##STR11##