# US 5,708,184 A · Process for the preparation of substituted aminocarbonyltriazolinones

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- Number: US 5,708,184 A
- Document ID: US5708184A
- Status: Granted
- Kind: A
- Application number: 08/686,079
- Filed: 1996-07-24
- Granted: 1998-01-13
- Earliest claimed: 1995-07-31
- Assignees: Bayer Aktiengesellschaft
- Inventors: Hans-Joachim Diehr
- Web page: https://patentgrep.com/patent/US5708184A

## CPC

- C07D 249/12: Oxygen or sulfur atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to a new process for the preparation of substituted amino-carbonyltriazolinones of the general formula (I) ##STR1## in which R.sup.1 and R.sup.2 have the meanings given in the description.

## Claims

### Claim 1

A process for the preparation of an aminocarbonyltriazolinone of the formula ##STR7## wherein R.sup.1 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino or C.sub.1 -C.sub.6 -dialkylamino, wherein each of which is optionally substituted by cyano, halogen or C.sub.1 -C.sub.4 -alkoxy,
R.sup.2 represents C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, or C.sub.2 -C.sub.12 -alkynyl, wherein said alkyl, alkenyl, or alkynyl groups are optionally substituted by cyano or halogen, or optionally substituted C.sub.3 -C.sub.6 -cycloalkyl, optionally substituted C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, optionally substituted phenyl-C.sub.1 -C.sub.4 -alkyl, or optionally substituted phenyl-C.sub.2 -C.sub.4 -alkynyl wherein said optional substituent is selected from the group consisting of cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 C.sub.4 -halogenalkoxy,
which consists essentially of reacting a triazolinone of the formula ##STR8## with an isocyanate of the formula
O.dbd.C.dbd.N--R.sup.2 (III)
in the presence of a reaction auxiliary, a basic compound and optionally a diluent, wherein said reaction auxiliary is metal compound selected from the corresponding hydride, hydroxide, acetate, carbonate, sulphate and halide of lithium, sodium, magnesium and aluminum and wherein said basic compound is an inorganic or organic base.

### Claim 2 (depends on 1)

The process according to claim 1, wherein
R.sup.1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- of t-butyl, n-, i-, s- or t-pentyI, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy,
R.sup.2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n-, i- or s-hexyl, propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl, each of which is optionally substituted by cyano, fluorine, chlorine or bromine, or represents cyclohexyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, benzyl; phenylethyl, phenylpropyl, phenylethenyl, phenylpropenyl, phenylethinyl or phenylpropinyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy or trifluoroethoxy.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the reaction is carried out in the presence of a diluent.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the reaction temperature is between 0.degree. and 150.degree. C.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the reaction is carried out under atmospheric pressure.

### Claim 6 (depends on 1)

The process according to claim 1, wherein between 0.9 to 1.5 mol of isocyanate, between 0.001 and 1 mol of the reaction auxiliary and between 0.001 and 1 mol of the basic compound is used per mol of the triazolinone of formula II.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the reaction auxiliary is lithium hydride, lithium hydroxide, lithium fluoride, lithium chloride and lithium bromide.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the reaction auxiliary is lithium chloride.

### Claim 9 (depends on 6)

The process according to claim 6 wherein the reaction auxiliary is lithium chloride and the basic compound is potassium hydroxide or 1,8-diazabicyclo›5,4,0!-undec-7-ene.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the reaction auxiliary is selected from the corresponding hydride, hydroxide, acetate, carbonate, sulphate, and halide of lithium, magnesium or aluminum.

### Claim 11 (depends on 1)

The process according to claim 1, wherein the substituted triazolinone of formula II, the reaction auxiliary and the basic compound are first placed in a diluent to form a mixture and the isocynate is then slowly metered into this mixture.