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O-Amidophenylmorpholine compounds and method of use
   
Document Number
US Patent 4123251
Issued Date
October 31, 1978
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Inventors
Shen; Kelvin K. (Fountain Valley, CA)
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Abstract
o-Amidophenylmorpholine compounds having a halo, haloalkyl, lower alkylsulfonyl, halo-lower alkylsulfonyl, or lower alkyl substituent on the aromatic ring para to the morpholino nitrogen. The compounds are useful as herbicides.
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Number of Claims:
16
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Published
October 31, 1978
Application Number
05/802,606
Filed
June 2, 1977
US Classification
504/224   544/159 544/166
Int'l Classification
A01N   43/72   (20060101)   A01N   43/84   (20060101)   C07D   295/135   (20060101)   C07D   295/00   (20060101)  
Examiner
Assistant Examiner
Attorney/Law Firm
USPTO Field of Search
544/166   544/159   71/88  
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5990309 - 2-chloro-5-fluoro-4-morpholinonitrobenzene and 2-chloro-5-fluoro-4-morpholinoaniline - Owned by Clariant GmbH (Frankfurt,DE)

The present invention relates to a process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkylaminoanilines, which comprises reacting, in a first step, an ortho-nitrochlorobenzene of the formula (1) in which X is Cl or F, with a secondary amine of the formula (2) HNR.sup.1 R.sup.2, in which R.sup.1 and R.sup.2, independently of one another, are identical or different and are an alkyl radical having from 1 to 10 carbon atoms or, together with the N atom to which they are bonded, form a ring having from 3 to 7 members, in the presence of a base in the presence or absence of a solvent at from -10 to 120.degree. C., reacting, in a second step, the 2-chloro-4-dialkylamino-5-fluoronitrobenzene with hydrogen at from 30 to 150.degree. C. and from 1 to 100 bar in the presence of a base and a noble-metal catalyst and, in a third step, extracting the 3-fluoro-4-dialkylaminoaniline from the reaction mixture using an aqueous solution of an acid as a salt dissolved in water, removing the aqueous phase and reacting the 3-fluoro-4-dialkylaminoaniline salt, dissolved in water, with a chloroformate of the formula (3) ClCO.sub.2 R.sup.3, in which R.sup.3 is an alkyl radical having from 1 to 10 carbon atoms or an aralkyl radical having from 7 to 20 carbon atoms, at from 0 to 100.degree. C. in the presence of a basic compound.

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