Claims
- 1. A method for the preparation of a benzamide which comprises reacting a benzoic acid represented by the formula (II) or (III) ##STR6## wherein R.sup.1 is an alkoxy group having 1 to 4 carbon atoms, a hydroxyl group or a hydrogen atom, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and selected from the group consisting of a hydrogen atom, a halogen atom, an alkoxy group, a nitro group, an alkyl group, an alkenyloxy group an amino group, a monoaklylamino group, a dialkylamino group, a cyano group, a sulfamoyl group, a monoalkylsulfamoyl group, a dialkylsulfamoyl group, a lower acyl group, a lower acylamido group; an alkylmercapto group, and a halomethyl group; and Z represents the carbon atoms necessary to complete a 5 to 7-membered ring, and R.sup.5 and R.sup.6 have the same definition as R.sup.2, R.sup.3 and R.sup.4 in formula (II) with N,N'-carbonyldiimidazole in an inert solvent to produce an intermediate, and reacting said intermediate with a solution of an amine having a primary and a secondary amino group of the formula (IA) or (IB) ##STR7## where W is a straight or branched chain alkylene group having 1 to 5 carbon atoms and m is 1 to 3, R.sup.7 is selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, a phenyl group and a benzyl group; wherein said amine is reacted in an equimolar or greater amount and said reaction is carried out at a temperature such that said intermediate selectively reacts with said primary amino group and does not substantially react with said secondary amino group.
- 2. The method of claim 1 wherein said amine is (S)-2-aminomethylpyrrolidine, (R)-2-aminomethylpyrrolidine or racemic 2-aminomethylpyrrolidine.
- 3. The method of claim 2 wherein said temperature is less than -15.degree. C.
- 4. The method of claim 1 wherein said acid is represented by the formula (II).
- 5. The method of claim 1 wherein said acid is represented by the formula (III).
- 6. The method of claim 4 wherein said acid is 4-amino-5-chloro-2-methoxybenzoic acid.
- 7. The method of claim 6 wherein said amine is (S)-2-aminomethylpyrrolidine.
- 8. The method of claim 5 wherein said acid is 5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid or 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid.
- 9. The method of claim 8 wherein said amine is (S)-2-aminomethylpyrrolidine.
- 10. The method of claim 3 wherein said temperature is in the range of approximately -30.degree. C. to -20.degree. C.
Parent Case Info
This is a continuation of co-pending application Ser. No. 115,014 filed Oct. 29, 1987, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4888353 |
Lednicer et al. |
Dec 1989 |
|
Non-Patent Literature Citations (1)
Entry |
Fieser & Fieser, "Reagents for Organic Synthesis"; vol. 1, (1967), pp. 114-116. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
115014 |
Oct 1987 |
|