# US 4,391,976 A · Process for producing arylsulfamates

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- Number: US 4,391,976 A
- Document ID: US4391976A
- Status: Granted
- Kind: A
- Application number: 06/313,064
- Filed: 1981-10-19
- Granted: 1983-07-05
- Earliest claimed: 1981-10-19
- Assignees: Ciba-Geigy Corporation
- Inventors: Beat Bohner
- Web page: https://patentgrep.com/patent/US4391976A

## CPC

- C07D 521/00: Heterocyclic compounds containing unspecified hetero rings
- C07D 251/16: to only one ring carbon atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A process for producing an N-(heterocyclo-aminocarbonyl)-arylsulfamate of the general formula I ##STR1## wherein R.sub.1 is hydrogen, methoxy or C.sub.1 -C.sub.3 -alkyl, R.sub.2 is hydrogen, fluorine, chlorine, bromine, nitro, CF.sub.3, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sub.3 is hydrogen, fluorine, chlorine, bromine, methyl or C.sub.1 -C.sub.4 -alkoxy, R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sub.5 is hydrogen, fluorine, chlorine, bromine, nitro or CF.sub.3, R.sub.6 is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, X is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl, methoxyethyl, CF.sub.3 or chlorine, Y is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl or methoxyethyl, and Z is the methine group or nitrogen, which process comprises adding, in an inert organic solvent, chlorosulfonylisocyanate of the formula III Cl--SO.sub.2 --N.dbd.C.dbd.O (III) to an aminoheterocyclic compound of the formula II ##STR2## wherein R.sub.1, X, Y and Z have the meanings defined under the formula I; and subsequently reacting this mixture, optionally with the addition of an agent binding hydrogen chloride, with a phenol of the formula IV ##STR3## wherein R.sub.2 and R.sub.3 have the meanings given under the formula I.

## Claims

### Claim 1

A process for producing an N-(heterocyclo-amino-carbonyl)-arylsulfamate of the formula I ##STR10## wherein R.sub.1 is hydrogen, methoxy or C.sub.1 -C.sub.3 -alkyl,
R.sub.2 is hydrogen, fluorine, chlorine, bromine, nitro, CF.sub.3, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl,
R.sub.3 is hydrogen, fluorine, chlorine, bromine, methyl or C.sub.1 -C.sub.4 -alkoxy,
R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl,
R.sub.5 is hydrogen, fluorine, chlorine, bromine, nitro or CF.sub.3,
R.sub.6 is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
X is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl, methoxyethyl, CF.sub.3 or chlorine,
Y is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl or methoxyethyl, and
Z is the methine group or nitrogen,
which process comprises adding, in an inert organic solvent, chlorosulfonylisocyanate of the formula III
Cl--SO.sub.2 --N.dbd.C.dbd.O
(III)
to an aminoheterocyclic compound of the formula II ##STR11## wherein R.sub.1, X, Y and Z have the meanings defined under the formula I; and subsequently reacting this mixture, optionally with the addition of an agent binding hydrogen chloride, with a phenol of the formula IV ##STR12## wherein R.sub.2 and R.sub.3 have the meanings given under the formula I.

### Claim 2 (depends on 1)

A process according to claim 1, wherein the reaction temperature is maintained between -10.degree. C. and +80.degree. C.

### Claim 3 (depends on 2)

A process according to claim 2, wherein the reaction temperature is between 0.degree. C. and +40.degree. C.

### Claim 4 (depends on 1)

A process according to claim 1, wherein cyclic or polyvalent ethers are used as solvent.

### Claim 5 (depends on 4)

A process according to claim 4, wherein the solvent is tetrahydrofuran, dioxane or dimethoxyethane.

### Claim 6 (depends on 1)

A process according to claim 1, performed in the presence of an agent binding hydrogen chloride, in which process carbonates or hydrogen carbonates of alkali metals or alkaline-earth metals, or tertiary amines, are used as binding agents.

### Claim 7 (depends on 6)

A process according to claim 6, wherein sodium or potassium carbonate, sodium or potassium hydrogen carbonate, pyridine or triethylamine are used.

### Claim 8 (depends on 1)

A process according to claim 1, wherein no agent binding hydrogen chloride is used.

### Claim 9 (depends on 1)

A process according to claim 1, wherein 1.0 to 1.3 mols of chlorosulfonylisocyanate per mol of the aminoheterocyclic compound are used.

### Claim 10 (depends on 9)

A process according to claim 9, wherein 1.0 to 1.2 mols of chlorosulfonylisocyanate are used.

### Claim 11 (depends on 1)

A process according to claim 1, which process comprises suspending the heterocycloamine of the formula II in absolute dioxane, adding at 5.degree.-10.degree. C., with cooling, 1.0 to 1.2 mols of chlorosulfonylisocyanate per mol of amine, introducing into the formed clear solution 0.9 to 1.0 mol of the phenol of the formula IV per mol of the aminoheterocyclic compound, optionally adding 1 mol of triethylamine in such a manner that the temperature of the reaction mixture does not exceed 25.degree. C., subsequently stirring the reaction mixture at 20.degree.-25.degree. C. until the reaction of the starting materials is completed, filtering the reaction mixture, concentrating the filtrate by evaporation, and finally isolating the product by crystallisation.