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Process for the preparation of N-aryl-N'-(mono- or di substituted)-urea derivatives

Assignee: Reanal Finomvegyszergyar Rt
•
Filing: 1981-01-23
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Granted: 1983-10-18
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Expires: 2001-01-23
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Abstract

Abstract The invention relates to a new method for the preparation of N-aryl-N'-(mono- or disubstituted)-urea derivatives having the general formula (I), ##STR1## wherein Aryl is an optionally substituted phenyl group, and R 1 and R 2 each stand for an optionally substituted alkyl, cycloalkyl, alkoxy or phenyl group, or R 1 and R 2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic group which may contain a further hetero atom, or one of R 1 and R 2 may also stand for hydrogen, with the proviso that if one of R 1 and R 2 is an optionally substituted phenyl group, the other may represent only hydrogen atom or an optionally substituted alkyl or alkoxy group, by reacting a carbamate of the general formula (II) with an amine of the general formula (III), R.sup.1 R.sup.2 N--CO--X (II) Aryl--NH.sub.2 (III) or a carbamate of the general formula (IV) with an amine of the general formula (V), Aryl--NH--CO--X (IV) R.sup.1 R.sup.2 NH (V) wherein R 1 , R 2 and Aryl are as defined above and X is a lower alkoxy, phenoxy or substituted phenoxy group, in the presence of a tertiary amine catalyst. According to the invention a tertiary alkylamine containing altogether at least 6 carbon atoms and minimum one alkyl chain with at least 4 carbon atoms or a mixture of such tertiary alkylamines is applied as catalyst.

Inventors

  • 👤 Sandor Torok
  • 👤 Lajos Voroshazy
  • 👤 Peter Galambos
  • 👤 Ivan Daroczi
  • 👤 Zoltan Ormenyi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 18:35
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; C07C; C07C273/00; C07C273/18; C07C273/1809; C07C273/1836; C07D295/00; C07D295/16; C07D295/20; C07D295/215

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 221 words
A process for the preparation of N-aryl-N'-(mono- or disubstituted)-urea derivatives having the formula (I), ##STR4## wherein Aryl is an optionally substituted phenyl group, and R 1 and R 2 each stand for an optionally substituted alkyl, cycloalkyl, alkoxy or phenyl group, or R 1 and R 2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic group which may contain a further hetero atom, or one of R 1 and R 2 may also stand for hydrogen, with the proviso that if one of R 1 and R 2 is an optionally substituted phenyl group, the other may represent only hydrogen atom or an optionally substituted alkyl or alkoxy group, by reacting a carbamate of the formula (II) with an amine of the formula (III), R.sup.1 R.sup.2 N--CO--X (II) Aryl--NH.sub.2 (III) or a carbamate of the general formula (IV) with an amine of the general formula (V), Aryl--NH--CO--X (IV) R.sup.1 R.sup.2 NH (V) wherein R 1 , R 2 and Aryl are as defined above and X is a lower alkoxy, phenoxy or substituted phenoxy group, in the presence of a tertiary amine catalyst, characterized in that a tertiary alkylamine containing altogether at least 6 carbon atoms and minimum one alkyl chain with at least 4 carbon atoms or a mixture of such tertiary alkylamines is applied as catalyst.
Claim 2
Dependent Claim 221 words
A process for the preparation of N-aryl-N'-(mono- or disubstituted)-urea derivatives having the formula (I), ##STR4## wherein Aryl is an optionally substituted phenyl group, and R 1 and R 2 each stand for an optionally substituted alkyl, cycloalkyl, alkoxy or phenyl group, or R 1 and R 2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic group which may contain a further hetero atom, or one of R 1 and R 2 may also stand for hydrogen, with the proviso that if one of R 1 and R 2 is an optionally substituted phenyl group, the other may represent only hydrogen atom or an optionally substituted alkyl or alkoxy group, by reacting a carbamate of the formula (II) with an amine of the formula (III), R.sup.1 R.sup.2 N--CO--X (II) Aryl--NH.sub.2 (III) or a carbamate of the general formula (IV) with an amine of the general formula (V), Aryl--NH--CO--X (IV) R.sup.1 R.sup.2 NH (V) wherein R 1 , R 2 and Aryl are as defined above and X is a lower alkoxy, phenoxy or substituted phenoxy group, in the presence of a tertiary amine catalyst, characterized in that a tertiary alkylamine containing altogether at least 6 carbon atoms and minimum one alkyl chain with at least 4 carbon atoms or a mixture of such tertiary alkylamines is applied as catalyst.
Claim 3
Dependent Claim 37 words
A process as set forth in claim 1, characterized in that a tertiary alkylamine containing at least one alkyl chain with at least 8 carbon atoms or a mixture of such tertiary alkylamines is applied as catalyst.
Claim 4
Dependent Claim 37 words
A process as set forth in claim 1 or 2, characterized in that the tertiary alkylamine catalyst is applied in an amount of 0.05-2 moles calculated for 1 mole of the reactant present in lower molar amount.
Claim 5
Dependent Claim 39 words
A process as set forth in any of claims 1 or 2, characterized in that the tertiary alkylamine catalyst is applied in an amount of 0.5-1.2 moles calculated for 1 mole of the reactant present in lower molar amount.
Claim 6
Dependent Claim 37 words
A process as set forth in claim 1 or 2, characterized in that the tertiary alkyl amine catalyst is selected from the group consisting of N,N-dimethyl-n-octylamine, N,N-dimethyl-n-dodecylamine, N,N-dimethyl-n-hexadecylamine, N,N-diethyl-n-oxtylamine, N,N-diethyl-n-dodecylamine, N,N-diethyl-n-hexadecyl, N-methyl-N-ethyl-n-octylamine, N-methyl-N-ethyl-n-dodecylamine, N-methyl-N-ethyl-n-hexadecylamine or mixtures thereof.

References Cited (Backward Citations)

US3555086A Cited
DE2617918A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-10-17 1987-04-18 1987-10-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-10-17 1991-04-18 1991-10-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-10-17 1995-04-18 1995-10-18 $7700.00 Window Closed / Lapsed

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