Method for making amides

Details Method for making amides Method for making amides

2000-08-10

2001-10-16

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S124000, C564S189000, C564S215000

Reexamination Certificate

active

06303817

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to amides, more specifically a method of making butanamides in a new process.
BACKGROUND OF THE INVENTION
U.S. Pat. Nos. 4,153,679 and 4,226,988, hereby incorporated by reference, disclose the use of paramenthane and acyclic carboxarnides as having a cooling effect on the skin and mucous membranes. These patents disclose the preparation and separation of the compounds through a three-step reaction sequence. The steps basically involve the hydrolysis of the compounds to an acid. The acid product is then reacted with thionyl chloride to form an acid chloride. The acid chloride is then reacted with an alkylamine to form carboxy amide
While this reaction is suitable for preparing the carboxamides, the process does not lend itself to the manufacture of the desired product in a simple economical process.
There is an ongoing need to provide the amides in high yield and in a simple, cost effective manner.
SUMMARY OF THE INVENTION
The invention a method for manufacturing amides of the formula
where Q is R
And where R is independently selected from hydrogen, (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkoxy, (C
2
-C
12
)alkenyl, halo(C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy (C
2
-C
12
)alkenyl, (C
1
-C
12
)alkoxy (C
2
-C
12
)alkynyl, (C
2
-C
12
)alkenyl(C
1
-C
12
)alkoxy, (C
2
-C
12
)alkynyl(C
1
-C
12
)alkoxy, (C
2
-C
12
)alkynyl (C
2
-C
12
)alkenyl, (C
2
-C
12
)alkenyl(C
2
-C
12
)alkynyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkenyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkynyl, (C
1
-C
12
) alkyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkenyl(C
3
-C
7
) cycloalkyl, (C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, halo(C
1
-C
12
)alkyl (C
3
-C
7
)cycloalkyl, halo(C
1
-C
12
) alkoxy(C
3
-C
7
)cycloalkyl, halo(C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, halo(C
2
-C
12
) alkynyl(C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)alkenyl(C
3
-C
7
)cycloalkyl, halo(C
2
-C
12
) alkynyl(C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)alkenyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
) alkoxy(C
1
-C
12
)alkyl (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl(C
3
-C
7
) cycloalkyl, (C
1
-C
12
)alkoxy (C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
) alkoxy (C
2
-C
12
)alkenyl(C
3
-C
7
) cycloalkyl, (C
2
-C
12
)alkenyl(C
1
-C
12
)alkoxy (C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
2
-C
12
)alkynyl(C
3
-C
7
) cycloalkyl, (C
2
-C
12
)alkynyl(C
1
-C
12
)alkoxy (C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkenyl(C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkynyl(C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
) cycloalkyl(C
3
-C
7
) cycloalkyl, (C
1
-C
12
)alkyl (C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkenyl (C
3
-C
7
)cycloalkyl (C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
3
-C
7
) cycloalkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl (C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl (C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkynyl (C
3
-C
7
)cycloalkyl, (C
3
-C
7
) cycloalkyl(C
1
-C
12
)alkoxy(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl (C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkenyl(C
3
-C
7
) cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkoxy(C
2
-C
12
) alkenyl(C
3
-C
7
)cycloalkyl, aryl, aralkyl, aryl(C
1
-C
12
)alkoxy, aryl(C
2
-C
12
)alkenyl, aryl (C
2
-C
12
)alkynyl, aryl(C
3
-C
7
)cycloalkyl, aryloxy(C
1
-C
12
)alkyl, aryloxy (C
2
-C
12
)alkynyl, aryloxy(C
2
-C
12
)alkenyl, aryl(C
1
-C
12
)alkoxy (C
3
-C
7
)cycloalkyl, aryl(C
2
-C
12
) alkenyl(C
3
-C
7
) cycloalkyl, aryl(C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, aryl(C
3
-C
7
) cycloalkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkylaryl, aryl(C
1
-C
4
)alkyl (C
3
-C
7
)cycloalkyl,heterocyclic, aryl (C
1
-C
4
)alkylheterocyclic, aryl(C
2
-C
4
)alkylheterocyclic, aryl (C
2
-C
4
)alkynylheterocyclic, heterocyclic (C
1
-C
4
)alkyl, and heterocyclic (C
3
-C
7
)cycloalkyl, (C
1
-C
6
)alkylphosphiny, (C
1
-C
6
)alkylphosphonyl, (C
1
-C
6
)alkylphosphonate, (C
1
-C
6
)alkylphosphite comprising:
Providing a nitrile compound of Formula II
where Q is preferably
or
and Q can be as defined above
and reacting the nitrile compound with the compound of Formula Ill hereinbelow:
where R is defined above
More specifically, the present invention is directed to the preparation of N,2,3-trimethyl-2-isoethyl-menthylbutanamide by the reaction of dimethylsulfate and disopropylpropionylnitrile. Another embodiment of the invention is directed to the preparation of N-2,3-trimethyl-2-ethylbutanarnide by the reaction of menthyl nitrile with diethyl sulfate.
The present reaction provides yields of the amide in commercially acceptable yields, in a single reaction step. In a highly preferred embodiment, diol and triol esters are employed as a solvent which has been found to increase reaction yields. These and other embodiments of the present invention will become apparent upon referring to the following description of the invention.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is based upon the discovery of a simple, efficient reaction to form the amide compounds recited herein. The preferred reaction products of the present invention are N-methyltrimethyl isopropyl butanamide and N-ethylmentyl carboxyamide. These amides are provided in a single reaction step by the reaction of a nitrile compound and a sulfate compound.
Suitable nitrile materials of formnula I include diisopropylpropionylnitrile, menthyl nitrile and the like.
The nitriles of Formula I are reacted with a sulfate compound of formula II, preferably selected from the group selected from dimethyl sulfate and diethyl sulfate.
The compounds of Formula I and II can be added in stoichiometric equal amounts. Preferably the level of dimethyl sulfate or diethyl sulfate is provided in stoichiometric excess so as to drive the reaction to higher yields of the resulting amide.
The aforementioned (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, (C
2
-C
12
)alkenyl, (C
2
-C
2
)alkynyl and (C
3
-C
7
)cycloalkyl groups may be optionally substituted with up to three substituents selected from the group consisting of nitro, trihalomethyl and cyano.
The term “alkyl” includes both branched and straight chain alkyl groups from 1 to 12 carbon atoms. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like. The term “haloalkyl” refers to an alkyl group substituted with 1 to 3 halogens.
The term “alkoxy” includes both branched and straight chain alkyl groups from 1 to 12 carbon atoms containing at least one oxygen atom. Typical alkoxy groups are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxyl, t-butoxy, n-pentoxy, isopentoxy, n-hexoxy, n-heptoxy and the like. The term “haloalkoxy” refers to an alkoxy group substituted with 1 to 3 halogens.
The term “alkenyl” refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 to 2 ethylenic bonds. The term “haloalkenyl” refers to an alkenyl group substituted with 1 to 3 halogen atoms.
The term “alkynyl” refers to an unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 to 2 acetylenic bonds. The term “halokynyl” refers to an alkynyl group substituted with 1 to 3 halogens.
The term “cycloalkyl” refers to a saturated ring system having 3 to 7 carbon atoms.
The term “aryl” includes phenyl or naphthyl, which may be substituted with up to three substituents independently selected from the group consisting of halogen, cyano, nitro, phenyl, phenoxy, (C
1
-C
6
)alkyl, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide, (C
1
-C
6
)alkoxy, and halo (C
1
-C
4
) alkyl.
Typical aryl substituents include, but are

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