Process for the preparation of diacylimides

• US 6,028,192 A
• Filed: 01/27/1998
• Issued: 02/22/2000
• Est. Priority Date: 01/31/1997
• Status: Expired due to Fees

• Current Assignee: Clariant GmbH (Clariant AG)
• Original Assignee: Clariant GmbH (Clariant AG)
• Inventors: Keil, Karl-Heinz, Delpy, Klaus, Mees, Bernhard, Becherer, Johannes
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): COLEMAN, BRENDA LIBBY
• Application Number:
  US09/013,756
• Time in Patent Office: 756 Days
• Field of Search: 564/152, 564/155, 564/159, 540/200, 540/362, 540/451, 540/529, 546/221, 546/245, 548/530, 548/539, 548/540
• US Class Current: 540/200
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C07C 233/91 with carbon atoms of the carboxamide groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 233/92 with at least one carbon atom of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07D 223/10 attached in position 2

Abstract

The present invention relates to a process for the preparation of compounds of the formula 1 ##STR1## by reacting a secondary acid amide of the formula 2 ##STR2## with an acid chloride of the formula 3 ##STR3## in the presence of N,N-diisopropyl-N-ethylamine. R¹, R² and R³ are alkyl or alkenyl radicals, if required also aryl radicals. The compounds of the formula 1 are suitable for use as insecticides or bleach activators.

Claims

1. A process for the preparation of compounds of the formula 1 ##STR8## where R¹ and R² are C₁ -C₂₄ -alkyl;

or C₂ -C₂ -alkenyl, or where R¹ and R² form a ring having 4 to 8 carbon atoms, and R³ is C₁ -C₂₄ -alkyl, C₂ -C₂₄ -alkenyl C₆ -C₁₄ -aralkyl or C₆ -C₁₄ -aryl

which comprises reacting a secondary acid amide of the formula 2 ##STR9## with at least one acid chloride of the formula 3 ##STR10## in the presence of only one basic compound N,N-diisopropyl-Nethylamine, said process is carried out without a solvent.

2. The process as claimed in claim 1, wherein R¹ and R² independently of one another are C₁ -C₁₀ -alkyl, C₂ -C₁₀ -alkenyl, it being possible for these radicals to be linear or branched.

3. The process as claimed in claim 1, wherein R₂ is methyl.

5. The process as claimed in claim 1, wherein R³ is linear or branched C₁ -C₄ -alkyl, C₆ -C₁₄ -aryl or C₆ -C₁₄ -aralkyl.

6. The process as claimed in claim 1, wherein R¹ and R² together form a ring which is substituted by an R⁴ radical, where R⁴ is C₁ -C₄ -alkyl or C₂ -C₄ -alkenyl.

7. The process as claimed in claim 1, wherein the acid chloride and the N,N-diisopropyl-N-ethylamine are used in a molar excess of in each case up to 10%, based on the secondary amide.

8. The process as claimed in claim 1, wherein the secondary amide is initially introduced and the acid chloride and the N,N-diisopropyl-N-ethylamine are added dropwise simultaneously, the temperature being maintained at between 25 and 150°

C., preferably 80 and 130°

C.

9. The process as claimed in claim 1, which comprises purifying the diacylimide by adding sufficient water to dissolve the hyrochloride of the N,N-diisopropyl-N-ethylamine formed during the reaction and separating it from the diacylimide by phase separation.

10. The process of claim 8 wherein said temperature is maintained between 80°

to 130°

C.

11. The process of claim 1 wherein R³ is benzyl or toluyl.

4. The process as claimed claim in 1, wherein R¹ and R² form a ring containing 7 atoms.