Title:
スルホン酸ジアミドの製法
Document Type and Number:
Japanese Patent JP5465672
Kind Code:
B2
Abstract:
The present invention relates to a process for preparing sulfuric diamides of the general formula I R1R2N—S(O)2—NH2 (I) in which R1 and R2 are each independently a primary alkyl radical having from 1 to 8 carbon atoms, a secondary alkyl radical having from 3 to 8 carbon atoms or a cycloalkyl radical having from 5 to 8 carbon atoms, or, together with the nitrogen atom, form a 5- to 8-membered, saturated nitrogen heterocycle which, as well as the nitrogen atom, may have a further heteroatom selected from O and S as a ring member, where the nitrogen heterocycle is unsubstituted or may have 1, 2, 3 or 4 alkyl groups having in each case from 1 to 4 carbon atoms as substituents. The process comprises the following steps: i) the reaction of a secondary amine of the formula II R1R2NH (II) in which R1 and R2 are each as defined above with sulfuryl chloride in an inert solvent, especially an aromatic solvent, in the presence of a tertiary amine to give a sulfamoyl chloride of the formula III R1R2N—S(O)2—Cl (III) in which R1 and R2 are each as defined above, and ii) reaction of the sulfamoyl chloride of the formula III obtained in step i) with ammonia, the sulfamoyl chloride of the formula III being used in step ii) in the form of the solution obtained in step i) in the inert solvent, especially the aromatic solvent.
Inventors:
Preshke, accelerator
Schmidt, thomas
Gebard, Joachim
Rail, sandra
Kyle, Michael
Wefels, Jan Hendrik
Schmidt, thomas
Gebard, Joachim
Rail, sandra
Kyle, Michael
Wefels, Jan Hendrik
Application Number:
JP2010528412A
Publication Date:
April 09, 2014
Filing Date:
October 10, 2008
Export Citation:
Assignee:
BASF SE
International Classes:
C07C303/38; C07C307/06; C07D239/54; A01N43/54; A01P13/00; C07B61/00
Domestic Patent References:
| JP2005530794A | ||||
| JP2006083133A | ||||
| JP2001523222A | ||||
| JP2005097138A | ||||
| JP5279210A | ||||
| JP2006504763A |
Foreign References:
| WO2006010474A1 | ||||
| US3198785 | ||||
| DE1240853B2 | ||||
| WO2001083459A1 |
Other References:
VANDI,A.,ET AL.,"Synthesis and Properties of Some N-Substituted Sulfamides",JOURNAL OF ORGANIC CHEMISTRY,1961年,VOL.26,NO.4,PP.1136-1138
BINKLEY,W. W.,ET AL.,"Organic Synthesis with Sulfuryl Chloride",JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,1939年12月,VOL.61,PP.3250-3251
AUDRIETH,L. F.,ET AL.,"Hydrazides of Sulfuric Acid and Their Derivatives. II. The Sulfamyl Hydrazides",JOURNAL OF ORGANIC CHEMISTRY,1956年 4月,VOL.21,NO.4,PP.426-428
ADKISON,K. K.,ET AL.,"Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?",BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS,2006年,VOL,16, NO.4,PP.978-983
BEHREND,R.,"Uber die Einwirkung von Sulfurylchlorid auf secundare Aminbasen",JUSTUS LIEBIGS ANNALEN DER CHEMIE,1883,VOL.222,PP.116-136
BINKLEY,W. W.,ET AL.,"Organic Synthesis with Sulfuryl Chloride",JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,1939年12月,VOL.61,PP.3250-3251
AUDRIETH,L. F.,ET AL.,"Hydrazides of Sulfuric Acid and Their Derivatives. II. The Sulfamyl Hydrazides",JOURNAL OF ORGANIC CHEMISTRY,1956年 4月,VOL.21,NO.4,PP.426-428
ADKISON,K. K.,ET AL.,"Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?",BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS,2006年,VOL,16, NO.4,PP.978-983
BEHREND,R.,"Uber die Einwirkung von Sulfurylchlorid auf secundare Aminbasen",JUSTUS LIEBIGS ANNALEN DER CHEMIE,1883,VOL.222,PP.116-136
Attorney, Agent or Firm:
Yusuke Hiraki
Ishii Teiji
Satoshi Fujita
Eiichi Arai
Ishii Teiji
Satoshi Fujita
Eiichi Arai