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US3883515A Expired / Lapsed US ⏱️ 0.0 years remaining

Adiabatic process for the production of 2,4-dichloro-6-amino-S-triazines

Assignee: Novartis Corp
•
Filing: 1973-03-14
•
Granted: 1975-05-13
•
Expires: 1993-03-14
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Abstract

Abstract A method for the production of 2,4-dichloro-6-mono substituted amino-s-triazines by reacting, in a solvent medium containing water, under substantially adiabatic conditions and for a relatively short period of time, cyanuric chloride with (a) a primary or secondary amine or (b) an amino compound containing in the molecule at least one water-solubilizing group such as a carboxylic acid or a sulfonic acid group. One group of products obtained by the process of the present invention are intermediates useful in the preparation of 2-chloro-4,6-diaminochloro-s-triazine products which are employed in inhibiting the growth of undesirable plants and are therefore extremely important and valuable for use as herbicides. Another group of compounds obtained by the present process are useful as intermediates in the production of optical brighteners or dyestuff components.

Inventors

  • 👤 Jai Prakash Tandon
  • 👤 William Sandford Durrell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 23:44
CPC Classifications
C; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/26; C07D251/40; C07D251/42; C07D251/46; C07D251/54; C07D251/70

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 139 words
A PROCESS FOR THE PREPARATION OF A 2,4-DICHLORO-6-MONOSUBSTITUTED AMINO-S-TRIAZINE WHICH COMPRISES A REACTING, UNDER ADIABATIC CONDITIONS AND IN A TWO-PHASE ORGANIC AQUEOUS SOLVENT MEDIUM, CYANURIC CHLORIDE WITH A. A PRIMARY OR SECONDARY AMINE OF THE FORMULA R1,R2,NH WHEREIN R1 IS A LOWER ALKYL, ALKENYL OR CYCLOALKYL RADICAL CONTAINING UP TO 6 CARBON ATOMS, R2 IS HYDROGEN, A LOWER ALKYLENE RADICAL THE CHAIN OF WHICH CAN BE SUBSTITUTED BY THE HYDROXYL GROUP OR BY HALOGEN OR WHICH CAN BE INTERRUPTED BY OXYGEN OR SULPHUR, R1 AND R2 TOGETHER WITH THE ADJACENT NITROGEN ATOM ALSO REPRESENT THE PYRROLIDINO, MORPHILINO, PYRIDAZINO, OR PIPERIDAZINO, RADICAL; OR B. AN AMINO COMPOUND CONTANING AT LEAST ONE WATERSOLUBILIZING GROUP SELECTED FROM AMONG CARBOXYLIC AND SULFONIC ACID GROUPS, SAID AMINO COMPOUND BEING SELECTED FROM AMONG AMINO-SUBSTITUTED STILBENE-2,2''DISULFONIC ACIDS, BENZENE SULFONIC ACIDS, NAPTHTALENESULFONIC ACIDS AND ANTRAQUININONE SULFONIC ACIDS.
Claim 2
Dependent Claim 139 words
A PROCESS FOR THE PREPARATION OF A 2,4-DICHLORO-6-MONOSUBSTITUTED AMINO-S-TRIAZINE WHICH COMPRISES A REACTING, UNDER ADIABATIC CONDITIONS AND IN A TWO-PHASE ORGANIC AQUEOUS SOLVENT MEDIUM, CYANURIC CHLORIDE WITH A. A PRIMARY OR SECONDARY AMINE OF THE FORMULA R1,R2,NH WHEREIN R1 IS A LOWER ALKYL, ALKENYL OR CYCLOALKYL RADICAL CONTAINING UP TO 6 CARBON ATOMS, R2 IS HYDROGEN, A LOWER ALKYLENE RADICAL THE CHAIN OF WHICH CAN BE SUBSTITUTED BY THE HYDROXYL GROUP OR BY HALOGEN OR WHICH CAN BE INTERRUPTED BY OXYGEN OR SULPHUR, R1 AND R2 TOGETHER WITH THE ADJACENT NITROGEN ATOM ALSO REPRESENT THE PYRROLIDINO, MORPHILINO, PYRIDAZINO, OR PIPERIDAZINO, RADICAL; OR B. AN AMINO COMPOUND CONTANING AT LEAST ONE WATERSOLUBILIZING GROUP SELECTED FROM AMONG CARBOXYLIC AND SULFONIC ACID GROUPS, SAID AMINO COMPOUND BEING SELECTED FROM AMONG AMINO-SUBSTITUTED STILBENE-2,2''DISULFONIC ACIDS, BENZENE SULFONIC ACIDS, NAPTHTALENESULFONIC ACIDS AND ANTRAQUININONE SULFONIC ACIDS.
Claim 3
Dependent Claim 20 words
A process according to claim 1 wherein the reaction is conducted in the presence of an alkali metal acid acceptor.
Claim 4
Dependent Claim 19 words
A process according to claim 2 wherein the alkali metal acid acceptor is an alkali metal hydroxide or carbonate.
Claim 5
Dependent Claim 19 words
A process according to claim 1 wherein the reaction is conducted at a temperature between about -8*C and 100*C.
Claim 6
Dependent Claim 20 words
A process according to claim 4 wherein the reaction is conducted at a temperature of about 25*C to about 85*C.
Claim 7
Dependent Claim 15 words
A process according to claim 1 wherein substantially stoichiometric amounts of the reactants are employed.
Claim 8
Dependent Claim 22 words
A process according to claim 1 wherein the cyanuric chloride is introduced into the reaction mixture in an inert organic solvent medium.
Claim 9
Dependent Claim 22 words
A process according to claim 7 wherein the solvent is selected from the group consisting of toluene, benzene, xylene, acetone and methylethylketone.
Claim 10
Dependent Claim 23 words
A process according to claim 2 wherein the alkali metal acid acceptor and amine are premixed and then reacted with the cyanuric chloride.
Claim 11
Dependent Claim 34 words
A process according to claim 1 wherein 2,4-dichloro-6-isopropylamino-s-triazine is obtained by reacting a toluene solution containing cyanuric chloride with isopropylamine in a two-phase organic/aqueous medium containing an alkali metal hydroxide or alkali metal carbonate.
Claim 12
Dependent Claim 14 words
A process according to claim 10 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 13
Dependent Claim 21 words
A process according to claim 11 wherein the isopropylamine, sodium hydroxide and water are premixed and then reacted with cyanuric chloride.
Claim 14
Dependent Claim 14 words
A process according to claim 10 wherein stoichiometric amounts of the reactants are employed.
Claim 15
Dependent Claim 19 words
A process according to claim 1 wherein the amino compound is 4,4''-diaminostilbene-2,2''-disulfonic acid or a water soluble salt thereof.
Claim 16
Dependent Claim 16 words
A process according to claim 14 wherein the water soluble salt is an alkali metal salt.
Claim 17
Dependent Claim 19 words
A process according to claim 14 wherein the reaction is conducted at a temperature between about -8* and 28*C.
Claim 18
Dependent Claim 20 words
A process according to claim 14 wherein the pH of the reacTion mixture is maintained between about 6 and 7.
Claim 19
Dependent Claim 18 words
A process according to claim 14 wherein the reaction is conducted in the presence of methylethylketone or acetone.
Claim 20
Dependent Claim 17 words
A process according to claim 14 wherein the reaction is conducted in the presence of sodium carbonate.

References Cited (Backward Citations)

US2459435A Cited
US3235359A Cited
US3403151A Cited
US3429881A Cited
US3459743A Cited
US3503971A Cited
US3505325A Cited
US3479349A Cited
US3681337A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-05-12 1978-11-11 1979-05-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-05-12 1982-11-11 1983-05-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-05-12 1986-11-11 1987-05-13 $7700.00 Window Closed / Lapsed

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