# US 5,350,859 A · Process for producing 3-hydroxymethyl-1-propargylimidazolidine-2,4-dione

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- Number: US 5,350,859 A
- Document ID: US5350859A
- Status: Granted
- Kind: A
- Application number: 08/020,739
- Filed: 1993-02-22
- Granted: 1994-09-27
- Earliest claimed: 1992-03-10
- Assignees: Sumotomo Chemical Company, Ltd.
- Inventors: Yoo Tanabe; Masanari Murakami; Hitomi Yamamoto
- Web page: https://patentgrep.com/patent/US5350859A

## CPC

- C07D 233/72: Two oxygen atoms, e.g. hydantoin
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed is a process for producing 3-hydroxymethyl-1-propargylimidazolidine-2,4-dione which comprises (i) reacting a compound of the formula (I) ##STR1## wherein R represents an alkyl, alkoxyalkyl or aralkyl group with a compound of the formula (II) CH.ident.C--CH.sub.2 --X (II) wherein X represents a leaving group in the presence of a base to give a 1-propargylimidazolidine-2,4-dione derivative of the formula (III) ##STR2## wherein R is as defined above and (ii) hydrolyzing this derivative of the formula (III).

## Claims

### Claim 1

A process for producing 3-hydroxymethyl-1-propargylimidazolidine -2,4-dione which comprises:
(i) reacting a compound of the formula (I) ##STR6## wherein R represents an alkyl, alkoxyalkyl or aralkyl group with a compound of the formula (II)
CH.ident.C--CH.sub.2 --X (II)
wherein X represents a halogen atom or sulfonic acid residue in the presence of a base to give a 1-propargylimidazolidine -2,4-dione derivative of the formula (III) ##STR7## wherein R is as defined above, and (ii) hydrolyzing this derivative of the formula (III).

### Claim 2 (depends on 1)

A process according to claim 1, wherein the hydrolysis in step (ii) is carried out in an aqueous solution of an acid.

### Claim 3 (depends on 1)

A process according to claim 1, wherein the base is alkali metal hydroxides or alkali metal carbonates.

### Claim 4 (depends on 1)

A process according to claim 1, wherein the reaction of step (i) is carried out in the presence of a phase transfer catalyst.

### Claim 5 (depends on 1)

A process according to claim 1, wherein the compound of the formula (II) and said base are used in an amount of about 1 to about 5 moles and about 1 to about 2 moles, respectively, per mole of the compound of the formula (I).

### Claim 6 (depends on 1)

A process according to claim 1, wherein the reaction in step (i) is carried out at a temperature within the range of about -10.degree. to about 50.degree. C. and the hydrolysis in step (ii) is carried out at a temperature within the range of about 20.degree. to about 100.degree. C.

### Claim 7

A process for producing 3-hydroxymethyl-1-propargylimidazolidine-2,4-dione which comprises:
(i) reacting imidazolidine-2,4-dione with a compound of the formula (IV)
Y--CH.sub.2 OR (IV)
wherein R represents an alkyl group, an alkoxyalkyl group or an aralkyl group and Y represents a halogen atom to obtain a compound of the formula (I): ##STR8## wherein R represents an alkyl, alkoxyalkyl or aralkyl group, (ii) reacting a compound of the formula (I) with a compound of the formula (II)
CH.ident.C--CH.sub.2 --X (II)
wherein X represents a halogen atom or sulfonic acid residue in the presence of a base to give a 1-propargylimidazolidine-2,4-dione derivative of the formula (III) ##STR9## wherein R is as defined above, and (iii) hydrolyzing this derivative of the formula (III).

### Claim 8 (depends on 1)

A process according to claim 1, wherein the halogen atom is chlorine, bromine or iodine and the sulfonic acid residue is --OSO.sub.2 R.sup.A wherein R.sup.A is C.sub.1 to C.sub.4 alkyl, phenyl or tolyl.

### Claim 9 (depends on 7)

A process according to claim 7 wherein the halogen atom is chlorine, bromine, or iodine.

### Claim 10 (depends on 1)

A process for producing 3-hydroxymethyl-1-propargylimidazolidine -2,4-dione according to claim 1, wherein R represents (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl, or phenyl substituted (C.sub.1 -C.sub.4) alkyl.

### Claim 11 (depends on 7)

A process for producing 3-hydroxymethyl-1-propargylimidazolidine -2,4-dione according to claim 7, wherein R represents (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl, or phenyl substituted (C.sub.1 -C.sub.4) alkyl.