- Preparation of 5-acylamino-1,2,4-triazole-3-sulfonamides
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5-Acylamino-1,2,4-triazole-3-sulfonamides, which are useful intermediates for the preparation of 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared from 5-amino-3-mercapto-1,2,4-triazole by sequential acylation to 5-acylamino-3-mercapto-1,2,4-triazoles, chlorination to 5-acylamino-3-chlorosulfonyl-1,2,4-triazoles, and condensation with substituted anilines to 5-acylamino-1,2,4-triazole-3-sulfonamides. 5-Acylamino-3-chlorosulfonyl-1,2,4-triazole compounds are key intermediates in the process.
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- New processes for the synthesis of 2,6-dichloro-3- methylaniline-Ph-UL-14C and methyl 6-chloroanthranilate-Ph-UL-14C
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Two new processes were developed for the synthesis of 2,6-dichloro-3-methylaniline-Ph-UL-14C (1), a key intermediate in the synthesis of a DowElanco experimental product presently being considered for commercialization. Both processes afford product in much higher yields than that previously reported in the literature. One of the processes was subsequenly applied to the synthesis of methyl 6-chloroanthranilate-Ph-14C (12), used as an intermediate for a second potential product.
- McKendry,Stanga
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p. 1157 - 1164
(2007/10/02)
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- Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines
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A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.
- Pews,Hunter,Wehrmeyer
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p. 4809 - 4820
(2007/10/02)
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- Process for the preparation of 2-chloro and 2,6-dichloroanilines
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2-Chloro and 2,6-dichloroanilines, optionally substituted in the 3-, 5-, and/or 6-position are prepared from the corresponding anilides by selective bromination, chlorination, reduction and hydrolysis. The selectivity of the process for introducing chlorines ortho to the amino group is very high.
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- A novel synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines
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2,6-Disubstituted and 2,3,6-trisubstituted anilines have been synthesized by a four-step approachy involving the selective reduction of a para halogen of the diacetanilide derivatives utilizing a palladium-on-carbon catalyst and formic acid salts as the in situ hydrogen donor.
- Pews,Hunter,Wehmeyer
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p. 7191 - 7194
(2007/10/02)
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