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US4348331A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of N-substituted imido-dicarboxylic acid diaryl esters

Assignee: Bayer AG
•
Filing: 1981-02-10
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Granted: 1982-09-07
•
Expires: 2001-02-10
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Abstract

Abstract This invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formula R.sup.1 --N(CO--OR.sup.2).sub.2 (I) wherein R 1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical, and R 2 is an optionally substituted aryl radical, which can be used as intermediates for the production of known herbicides, which process comprises reacting an amine salt of the formula R.sup.1 --NH.sub.2.HX.sup.1 (II) wherein X 1 is a halogen, with a carbonic acid aryl ester halide of the formula R.sup.2 --O--CO--X.sup.2 (III) wherein X 2 is halogen, at a temperature from 100° C. to 300° C.

Inventors

  • 👤 Karlfried Dickore
  • 👤 Engelbert Kuhle

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 22:52
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/64; C; C07; C07C; C07C271/00; C07C271/62; C07C271/66; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/38; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52; C07D309/00; C07D309/02; C07D309/04

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 222 words
Process for the production of an N-substituted imido-dicarboxylic acid diaryl ester compound of the formula R.sup.1 -N(CO-OR.sup.2).sub.2 (I) wherein R 1 is a straight-chain or branched alkyl of from 1 to 10 carbon atoms; substituted alkyl wherein the substituents are at least one of lower alkoxy, lower alkylmercapto, halogen, cyano or nitro; alkenyl or alkynyl of from 3 to 8 carbon atoms; cycloaliphatic of from 3 to 8 carbon atoms; substituted by cycloaliphatic wherein the substituent is lower alkyl; araliphatic with from 7 to 12 carbon atoms; substituted araliphatic wherein the aromatic ring system is substituted by halogen, nitro, trifluoromethyl, cyano, lower alkyl or lower alkoxy; an aromatic radical of from 6 to 12 carbon atoms and is optionally substituted by halogen, nitro, trifluoromethyl, cyano, lower alkyl or lower alkoxy; R 2 is a phenyl or naphthyl radical; substituted phenyl or naphthyl wherein the substituents are at least one of chlorine, methyl or methoxy; and which process comprises reacting an amine salt of the formula R.sup.1 -NH.sub.2 HX.sup.1 (I) in which R 1 is defined as above; and X 1 is a chlorine atom with a carbonic acid aryl ester halide of the formula R.sup.2 O--CO--X.sup.2 (III) wherein R 2 is defined as above; and X 2 is a chlorine or fluorine atom at a temperature from 100° C. to 300° C.
Claim 2
Dependent Claim 222 words
Process for the production of an N-substituted imido-dicarboxylic acid diaryl ester compound of the formula R.sup.1 -N(CO-OR.sup.2).sub.2 (I) wherein R 1 is a straight-chain or branched alkyl of from 1 to 10 carbon atoms; substituted alkyl wherein the substituents are at least one of lower alkoxy, lower alkylmercapto, halogen, cyano or nitro; alkenyl or alkynyl of from 3 to 8 carbon atoms; cycloaliphatic of from 3 to 8 carbon atoms; substituted by cycloaliphatic wherein the substituent is lower alkyl; araliphatic with from 7 to 12 carbon atoms; substituted araliphatic wherein the aromatic ring system is substituted by halogen, nitro, trifluoromethyl, cyano, lower alkyl or lower alkoxy; an aromatic radical of from 6 to 12 carbon atoms and is optionally substituted by halogen, nitro, trifluoromethyl, cyano, lower alkyl or lower alkoxy; R 2 is a phenyl or naphthyl radical; substituted phenyl or naphthyl wherein the substituents are at least one of chlorine, methyl or methoxy; and which process comprises reacting an amine salt of the formula R.sup.1 -NH.sub.2 HX.sup.1 (I) in which R 1 is defined as above; and X 1 is a chlorine atom with a carbonic acid aryl ester halide of the formula R.sup.2 O--CO--X.sup.2 (III) wherein R 2 is defined as above; and X 2 is a chlorine or fluorine atom at a temperature from 100° C. to 300° C.
Claim 3
Dependent Claim 21 words
Process as claimed in claim 1 wherein the reaction is carried out at a temperature of between 170° and 250° C.
Claim 4
Dependent Claim 18 words
Process as claimed in claim 1 wherein the reaction is carried out in the presence of a diluent.
Claim 5
Dependent Claim 24 words
Process as claimed in claim 1 wherein the carbonic acid aryl ester halide of formula (III) is employed in a greater than stoichiometric amount.
Claim 6
Dependent Claim 18 words
Process as claimed in claim 1 wherein R 1 is alkyl of from 1 to 10 carbon atoms.
Claim 7
Dependent Claim 30 words
Process as claimed in claim 1 wherein R 1 is substituted alkyl, wherein the substituents are selected from the group consisting of lower alkoxy, lower alkylmercapto, halogen, cyano or nitro.
Claim 8
Dependent Claim 20 words
Process as claimed in claim 1 wherein R 1 is alkenyl or alkynyl with from 3 to 8 carbon atoms.
Claim 9
Dependent Claim 18 words
Process as claimed in claim 1 wherein R 1 is cycloaliphatic with from 3 to 8 carbon atoms.
Claim 10
Dependent Claim 20 words
Process as claimed in claim 1 wherein R 1 is substituted cycloaliphatic wherein the substituents are selected from lower alkyl.
Claim 11
Dependent Claim 20 words
Process as claimed in claim 1 wherein R 1 is an araliphatic radical with from 7 to 12 carbon atoms.
Claim 12
Dependent Claim 30 words
Process as claimed in claim 1 wherein R 1 is a substituted araliphatic radical wherein the aromatic ring is substituted by halogen, nitro, trifluoromethyl, cyano, lower alkyl and lower alkoxy.
Claim 13
Dependent Claim 20 words
Process as claimed in claim 1 wherein R 1 is an aromatic radical of from 6 to 12 carbon atoms.
Claim 14
Dependent Claim 33 words
Process as claimed in claim 1 wherein R 1 is a substituted aromatic radical wherein the substituents are selected from the group consisting of halogen, nitro, trifluoromethyl, cyano, lower alkyl and lower alkoxy.
Claim 15
Dependent Claim 11 words
Process as claimed in claim 1 wherein R 2 is phenyl.
Claim 16
Dependent Claim 25 words
Process as claimed in claim 1 wherein R 2 is a substituted phenyl wherein the substituents are at least one of chlorine, methyl or methoxy.
Claim 17
Dependent Claim 11 words
Process as claimed in claim 1 wherein R 2 is naphthyl.
Claim 18
Dependent Claim 24 words
Process as claimed in claim 1 wherein R 2 is substituted naphthyl wherein the substituents are at least one of chlorine, methyl or methoxy.
Claim 19
Dependent Claim 17 words
Process as claimed in claim 1 wherein neopentylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 20
Dependent Claim 17 words
Process as claimed in claim 1 wherein sec.-butylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 21
Dependent Claim 17 words
Process as claimed in claim 1 wherein isobutylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 22
Dependent Claim 17 words
Process as claimed in claim 1 wherein neopentylamine hydrochloride is reacted with carbonic acid tolyl ester chloride.
Claim 23
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2-aminohexane hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 24
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2,2-dimethyl-1-aminobutane hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 25
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2,4-dimethyl-3-aminopentane hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 26
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2-ethyl-hexylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 27
Dependent Claim 17 words
Process as claimed in claim 1 wherein 3-aminopentane hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 28
Dependent Claim 17 words
Process as claimed in claim 1 wherein 3-amino-1-propylene hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 29
Dependent Claim 17 words
Process as claimed in claim 1 wherein cyclopentylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 30
Dependent Claim 17 words
Process as claimed in claim 1 wherein cyclohexylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 31
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2-(bicyclo[2.2.1]-heptyl)-methylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 32
Dependent Claim 17 words
Process as claimed in claim 1 wherein 2,2,2-trifluoroethylamine hydrochloride is reacted with carbonic acid phenyl ester chloride.
Claim 33
Dependent Claim 17 words
Process as claimed in claim 1 wherein 1,1,1-trifluoro-2-aminopropane hydrochloride is reacted with carbonic acid phenyl ester chloride.

References Cited (Backward Citations)

US1527868A Cited
GB484683A Cited
US2395750A Cited
US2541646A Cited
US2522393A Cited
US3555076A Cited
US4014923A Cited
US4056527A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-09-06 1986-03-08 1986-09-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-09-06 1990-03-08 1990-09-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-09-06 1994-03-08 1994-09-07 $7700.00 Window Closed / Lapsed

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