2-oxo-1,3-dioxolane-4-acyl halides, their preparation and use

Patent metadata

Field	Value
Publication number	US-9643948-B2
Application number	US-201414899638-A
Country	US
Kind code	B2
Filing date	May 15, 2014
Priority date	Jun 26, 2013
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

The present invention suggests 2-oxo-1,3-dioxolane-4-acyl halides of formula (I),

wherein X is selected from F, Cl, Br, I and mixtures thereof, preferably Cl, processes for the preparation of said 2-oxo-1,3-dioxolane-4-acyl halides, the use of said 2-oxo-1,3-dioxolane-4-acyl halides for the preparation of 2-oxo-1,3-dioxolane-4-carboxylic esters of formula (II),

the use of said 2-oxo-1,3-dioxolane-4-acyl halides for the preparation of 2-oxo-1,3-dioxolane-4-carboxamides of formula (III),

and also the use of said 2-oxo-1,3-dioxolane-4-acyl halides as agents for the blocking of amines.

First claim

The invention claimed is:

1. 2-Oxo-1,3-dioxolane-4-acyl halide of formula (I),

wherein X is selected from F, Cl, Br, I and mixtures thereof.

2. The 2-Oxo-1,3-dioxolane-4-acyl halide according to claim 1 , wherein X is Cl.

3. A process for the preparation of the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 , wherein 2-oxo-1,3-dioxolane-4-carboxylic acid of formula (X)

is reacted with an halogenation agent.

4. The process according to claim 3 , wherein the halogenation agent is SOCl 2 .

5. The process according to claim 4 , wherein the reaction is carried out without a solvent at an elevated temperature.

6. The process according to claim 5 , wherein the halogenation is carried out at about 60° C. in the presence of dimethylformamide as a catalyst.

7. A process comprising reacting the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 with an alcohol R 1 —OH for the preparation of a 2-oxo-1,3-dioxolane-4-carboxylic ester of formula (II),

wherein R 1 is selected from straight-chain C 1-12 -alkyl groups, branched or cyclic C 3-12 -alkyl groups, C 6-10 -aryl groups, C 6-12 -aralkyl groups and C 6-12 -alkaryl groups.

8. A process comprising reacting the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 with a multifunctional polyol comprising R 1 for the preparation of a 2-oxo-1,3-dioxolane-4-carboxylic ester of formula (II),

wherein R 1 is a radical having a valency of 2 to 6, which is substituted with 1 to 5 further 2-oxo-1,3-dioxolane-4-carboxylic ester groups.

9. A process comprising reacting the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 with an amine NH 2 R 1 for the preparation of a 2-oxo-1,3-dioxolane-4-carboxamide of formula (III),

wherein R 1 and R 2 , in each case independently of one another, are selected from H, straight-chain C 1-12 -alkyl groups, branched or cyclic C 3-12 -alkyl groups, C 6-10 -aryl groups, C 6-12 -aralkyl groups and C 6-12 -alkaryl groups or, together with the N atom to which they are bonded, form a 5- to 8-membered ring.

10. A process comprising reacting the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 with a multifunctional amine comprising R 2 for the preparation of a 2-oxo-1,3-dioxolane-4-carboxamide of formula (III),

wherein R 1 is selected from H, straight-chain C 1-12 -alkyl groups, branched or cyclic C 3-12 -alkyl groups, C 6-10 -aryl groups, C 6-12 -aralkyl groups, C 6-12 -alkaryl groups, or a polypeptide residue, and R 2 is a radical having a valency of 2 to 6, which is substituted with 1 to 5 further 2-oxo-1,3-dioxolane-4-carboxamide groups.

11. A process comprising blocking an amine by reaction with the 2-oxo-1,3-dioxolane-4-acyl halide as defined in claim 1 .

Assignees

• Construction Research & Technology Gmbh
• Construction Research & Technology Gmbh

Inventors

• Putzien Sophie
• Köhler Maximilian
• Wölfle Heimo
• Walther Burkhard

Classifications

• C07D317/36 Primary

  Alkylene carbonates; Substituted alkylene carbonates · CPC title

• C07B41/08

  of carboxyl groups or salts, halides or anhydrides thereof · CPC title