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Process for the preparation of (thio)hydantoins substituted with amide groups

Assignee: Bayer AG
•
Filing: 1978-04-19
•
Granted: 1979-10-02
•
Expires: 1998-04-19
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Abstract

Abstract A process for the preparation of an amide-substituted (thio)hydantoin which comprises reacting a primary mono- or poly-amine with an optionally substituted maleic acid amide reacting the resulting product with an organic mono- or poly-iso(thio)cyanate and subsequently cyclizing the resulting product by the action of heat.

Inventors

  • 👤 Ludwig Rottmaier
  • 👤 Rudolf Merten

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 06:11
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/86; C07D233/72; C07D233/76; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3821; C08G73/00; C08G73/06; C08G73/0605; C08G73/0616

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 92 words
Processes for the preparation of amide-substituted (thio)hydantoins which comprises reacting a primary mono- or poly-amine with a maleic acid amide corresponding to the following general formula (I): wherein R 1 , r 2 and R 6 , which may be the same or different, each represents hydrogen or an optionally substituted aliphatic radical; R 5 represents hydrogen or an optionally substituted aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic radical; and k represents an integer of from 1 to 3; reacting the resulting product with an organic mono- or poly-iso(thio)cyanate and subsequently cyclising the
Claim 2
Dependent Claim 92 words
Processes for the preparation of amide-substituted (thio)hydantoins which comprises reacting a primary mono- or poly-amine with a maleic acid amide corresponding to the following general formula (I): wherein R 1 , r 2 and R 6 , which may be the same or different, each represents hydrogen or an optionally substituted aliphatic radical; R 5 represents hydrogen or an optionally substituted aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic radical; and k represents an integer of from 1 to 3; reacting the resulting product with an organic mono- or poly-iso(thio)cyanate and subsequently cyclising the
Claim 3
Dependent Claim 151 words
Processes as claimed in claim 1 in which, in general formula (I), R 1 , R 2 and R 6 represents hydrogen or a C 1 -C 18 alkyl radical optionally substituted by halogen, R 5 represents hydrogen, a C 1 -C 20 alkyl radical, a C 5 -C 12 cycloalkyl radical which both may optionally be substituted by halogen, by a hydroxy, by C 1 -C 18 alkoxy, by C 2 -C 18 alkoxy carbonyl group or by a hydroxy carbonyl group, a C 6 -C 16 aryl radical which may optionally be substituted by halogen, nitro group by C 1 -C 18 alkyl, by C 1 -C 18 haloalkyl, hydroxy, by C 1 -C 18 hydroxyalkoxy, by C 2 -C 18 alkoxy carbonyl or by hydroxy carbonyl groups, a C 7 -C 18 aralkyl radical or a C 5 -C 12 heterocyclic radical containing N, O and/or S-atoms in
Claim 4
Dependent Claim 12 words
Processes as claimed in claim 2, wherein R 5 represents hydrogen, a
Claim 5
Dependent Claim 38 words
Processes as claimed in claim 1, wherein the maleic acid amides are maleic acid mono amide, N-methyl, N-butyl, N-phenyl maleic acid mono amide, bis-amide acid mono amide based on hexamethylene diamine, diaminodiphenyl methane, phenylene diamine, tolylene diamine or
Claim 6
Dependent Claim 12 words
Processes as claimed in claim 1 wherein the cyclisation is carried out
Claim 7
Dependent Claim 38 words
Processes as claimed in claim 1 wherein the primary mono- or polyamine corresponds to the following general formula (III): r.sub.3 --nh.sub.2 ].sub.1 (ii) wherein R 3 represents an optionally substituted aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic radical; and
Claim 8
Dependent Claim 28 words
Processes as claimed in claim 6 in which, in general formula (II), l represents 1 or 2, R 3 has the meaning of R 5 , except for
Claim 9
Dependent Claim 37 words
Processes as claimed in claim 7, wherein R 3 represents a C 1 -C 18 alkyl radical, C 5 or C 6 cycloalkyl radical or a C 1 -C 16 aryl radical optionally substituted by halogen, by
Claim 10
Dependent Claim 49 words
Processes as claimed in claim 1 wherein the mono- or poly-iso(thio)cyanate corresponds to one of the following general formulae (III): r.sub.4 (--nco).sub.z and R.sub.4 (--NCS).sub.z (III) wherein R 4 represents an optionally substituted aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic radical, excluding the substituent hydroxy, hydroxyalkoxy and hydroxy carbonyl; and
Claim 11
Dependent Claim 12 words
Processes as claimed in claim 9 wherein in general formulae (III), z
Claim 12
Dependent Claim 72 words
Processes as claimed in claim 9, wherein R 4 represents an aliphatic C 1 -C 20 radical which may optionally be substituted by halogen, by C 1 -C 6 alkyl and/or by C 6 -C 16 aryl groups, a C 6 -C 16 aromatic radical, a C 5 -C 12 cycloaliphatic radical, a C 7 -C 20 aliphatic-aromatic radical or a C 5 -C 12 aromatic or cycloaliphatic radical containing a hetero
Claim 13
Dependent Claim 26 words
Processes as claimed in claim 1 wherein the reaction between the amine and the acid amide is carried out at a temperature of from -20° to
Claim 14
Dependent Claim 22 words
Processes as claimed in claim 1 wherein the reaction of the iso(thio)cyanate is carried out at a temperature of from -20° to
Claim 15
Dependent Claim 12 words
Processes as claimed in claim 13 wherein the said temperature is from
Claim 16
Dependent Claim 13 words
Processes as claimed in claim 1 wherein cyclisation is carried out at a
Claim 17
Dependent Claim 12 words
Processes as claimed in claim 15 wherein the said temperature is from
Claim 18
Dependent Claim 10 words
An amide-substituted (thio) hydantoin when prepared by a process as
Claim 19
Dependent Claim 10 words
An amide-substituted (thio) hydantoin when prepared by a process as
Claim 20
Dependent Claim 13 words
A lacquer composition comprising an amide-substituted (thio) hydantoin as claimed in claim 17.

References Cited (Backward Citations)

US3549599A Cited
US4089860A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-10-01 1983-04-02 1983-10-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-10-01 1987-04-02 1987-10-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-10-01 1991-04-02 1991-10-02 $7700.00 Window Closed / Lapsed

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