# US 5,705,651 A · Process for producing a 3,4-alkylene-1,3,4-thiadiazolidin-2-one and intermediates for the same

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- Number: US 5,705,651 A
- Document ID: US5705651A
- Status: Granted
- Kind: A
- Application number: 08/517,676
- Filed: 1995-08-22
- Granted: 1998-01-06
- Earliest claimed: 1994-08-22
- Assignees: Mitsubishi Chemical Corporation
- Inventors: Chikako Ota; Bunji Natsume
- Web page: https://patentgrep.com/patent/US5705651A

## CPC

- C07D 285/135: Nitrogen atoms
- C07C 337/06: Compounds containing any of the groups [IMAGE cpc-sch-C07C-0987.gif], e.g. thiosemicarbazides
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

According to the process of the present invention, a 3,4-alkylene-1,3,4-thiadiazolidin-2-one, which is useful as a herbicide, can be easily produced in a high yield by reacting a 1,3,4-thiadiazolidin-2-one with a dihaloalkane in the presence of a base.

## Claims

### Claim 1

A process for producing 3,4-alkylene-1,3,4-thiadiazolidin-2-one represented by the formula (III): ##STR7## wherein R.sup.1 represents a hydrogen atom or an inert substituent; R.sup.2 represents a halogen atom, a nitro group, a methyl group or a methoxy group; R.sup.3 represents a hydrogen atom or a halogen atom; and n represents an integer of from 3 to 5, which comprises reacting a 1,3,4-thiadiazolidin-2-one represented by the formula (I): ##STR8## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined above, with a dihaloalkane represented by the formula (II):
X(CH.sub.2).sub.n X (II)
wherein X represents a halogen atom; and n is as defined above, in the presence of a base.

### Claim 2 (depends on 1)

A process as claimed in claim 1, wherein said 1,3,4-thiadiazolidin-2-one is obtained by hydrolyzing a 3-formyl-1,3,4-thiadiazolidin-2-one represented by the formula (IV): ##STR9## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined in claim 1.

### Claim 3 (depends on 1, 2)

A process as claimed in claim 2, wherein said 3-formyl-1,3,4-thiadiazolidin-2-one is obtained by reacting a thiosemicarbazide represented by the formula (V): ##STR10## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined in claim 1, with phosgene.

### Claim 4 (depends on 1, 3)

A process as claimed in claim 3, wherein said thiosemicarbazide is obtained by reacting an isothiocyanate represented by the formula (VI): ##STR11## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined in claim 1, with formhydrazide.

### Claim 5 (depends on 1)

A process as claimed in claim 1, wherein R.sup.1 is a group represented by --ACH.sub.2 CO.sub.2 R.sup.4, in which A is an oxygen atom or a sulfur atom and R.sup.4 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a tetrahydrofuryl group substituted by an acyloxy group having 2 to 5 carbon atoms; R.sup.2 is a halogen atom; R.sup.3 is a hydrogen atom or a halogen atom; and n is an integer of from 3 to 5.

### Claim 6 (depends on 2)

A process as claimed in claim 2, wherein R.sup.1 is a group represented by --ACH.sub.2 CO.sub.2 R.sup.4, in which A is an oxygen atom or a sulfur atom and R.sup.4 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a tetrahydrofuryl group substituted by an acyloxy group having 2 to 5 carbon atoms; R.sup.2 is a halogen atom; R.sup.3 is a hydrogen atom or a halogen atom; and n is an integer of from 3 to 5.

### Claim 7 (depends on 3)

A process as claimed in claim 3, wherein R.sup.1 is a group represented by --ACH.sub.2 CO.sub.2 R.sup.4, in which A is an oxygen atom or a sulfur atom and R.sup.4 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a tetrahydrofuryl group substituted by an acyloxy group having 2 to 5 carbon atoms; R.sup.2 is a halogen atom; R.sup.3 is a hydrogen atom or a halogen atom; and n is an integer of from 3 to 5.

### Claim 8 (depends on 4)

A process as claimed in claim 4, wherein R.sup.1 is a group represented by --ACH.sub.2 CO.sub.2 R.sup.4, in which A is an oxygen atom or a sulfur atom and R.sup.4 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a tetrahydrofuryl group substituted by an acyloxy group having 2 to 5 carbon atoms; R.sup.2 is a halogen atom; R.sup.3 is a hydrogen atom or a halogen atom; and n is an integer of from 3 to 5.

### Claim 9 (depends on 1)

A process as claimed in claim 1, wherein R.sup.1 is a group represented by --SCH.sub.2 CO.sub.2 R.sup.4, in which R.sup.4 is a methyl group or a 4-acetoxytetrahydrofruan-3-yl group; R.sup.2 is a chlorine atom; R.sup.3 is a fluorine atom; and n is an integer of 3 or 4.

### Claim 10 (depends on 2)

A process as claimed in claim 2, wherein R.sup.1 is a group represented by --SCH.sub.2 CO.sub.2 R.sup.4, in which R.sup.4 is a methyl group or a 4-acetoxytetrahydrofruan-3-yl group; R.sup.2 is a chlorine atom; R.sup.3 is a fluorine atom; and n is an integer of 3 or 4.

### Claim 11 (depends on 3)

A process as claimed in claim 3, wherein R.sup.1 is a group represented by --SCH.sub.2 CO.sub.2 R.sup.4, in which R.sup.4 is a methyl group or a 4-acetoxytetrahydrofruan-3-yl group; R.sup.2 is a chlorine atom; R.sup.3 is a fluorine atom; and n is an integer of 3 or 4.

### Claim 12 (depends on 4)

A process as claimed in claim 4, wherein R.sup.1 is a group represented by --SCH.sub.2 CO.sub.2 R.sup.4, in which R.sup.4 is a methyl group or a 4-acetoxytetrahydrofruan-3-yl group; R.sup.2 is a chlorine atom; R.sup.3 is a fluorine atom; and n is an integer of 3 or 4.