- A New Method for the Synthesis of Heterocyclic S-Alkyl Thiolactams
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The reaction of S-substituted heterocyclic thiolactams with thiols is described.In some cases, rearrangement or tricyclic products were produced instead of the compounds expected from simple alkylthiol displacement.
- Jackman, Dennis E.,Westphal, Dietmar B.
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p. 1134 - 1136
(2007/10/02)
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- Production of S-substituted isothioureas
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A process for the production of an S-substituted isothiourea including the functional group STR1 in which R1 is an alkyl, alkenyl, aryl or aralkyl radical, comprising reacting a thiourea including the functional group STR2 with an alpha-activated etherifying agent of the formula in which X is a halogen atom, A is a direct bond or CH2, and Y is an electron withdrawing group, thereby to produce the ether STR3 and in a second step reacting the ether with a compound of the formula R1 SH. The process is particularly applicable to the production of the known herbicide STR4 from the corresponding thiourea where in the first step chloroacetic acid is used to form the S- carboxymethyl isothiourea which is then interchanged with ethyl mercaptan. Higher overall yields and/or economies are thereby achieved.
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