Production method for compound comprising amino group and/or hydroxyl group

Patent metadata

Field	Value
Publication number	US-9278905-B2
Application number	US-201314382455-A
Country	US
Kind code	B2
Filing date	Mar 4, 2013
Priority date	Mar 2, 2012
Publication date	Mar 8, 2016
Grant date	Mar 8, 2016

Abstract

Disclosed is a method for producing a compound having an amino group and/or a hydroxyl group from a substrate compound having an atomic group containing CO or CS by eliminating such atomic group. The substrate compound, having an atomic group containing CO or CS (for example, an amide, a carbamate, or the like), is allowed to react with a compound expressed by formula (I) below, at a temperature of 120° C. or lower, preferably in the presence of an ammonium salt, to eliminate such atomic group containing CO or CS. In formula (I) A may not be present, and in a case where A is present, A represents an alkyl group having 1 to 6 carbon atoms.

H 2 N-A-NH 2   (I).

First claim

The invention claimed is:

1. A method for producing a first compound having at least one of an amino group and a hydroxyl group from a substrate compound having an atomic group containing a carbonyl or thiocarbonyl group CX, wherein X represents an oxygen atom or a sulfur atom, the method comprising allowing said substrate compound to react with a second compound in the presence of an ammonium salt at a temperature of 120° C. or lower to eliminate said atomic group containing the CX from said substrate compound, said second compound being expressed by formula (I):
H 2 N-A-NH 2   (I)

wherein A represents:
a bond; or
an unsubstituted alkylene group having 1 to 6 carbon atoms; or
a substituted alkylene group, in which one or two of the carbon atoms of an unsubstituted alkylene group having 2 to 6 carbon atoms is each substituted with a nitrogen atom.

2. The method as claimed in claim 1 , wherein the ammonium salt is an ammonium halide.

3. The method as claimed in claim 2 , wherein the substrate compound is an amide, the atomic group containing CX is an N-acyl group, and the reaction is carried out by eliminating the acyl group to produce the first compound from said substrate compound, the first compound having the amino group.

4. The method as claimed in claim 3 , wherein the second compound is hydrazine.

5. The method as claimed in claim 3 , wherein the second compound is an alkylenediamine.

6. The method as claimed in claim 5 , wherein the alkylenediamine is ethylenediamine.

7. The method as claimed in claim 1 , wherein the substrate compound is a cyclic carbamate, a chain carbamate, a cyclic carbonate, a chain carbonate, a cyclic urea or a chain urea, the atomic group containing CX is a carbonyl group, and the reaction of the substrate compound with an alkylenediamine as the second compound eliminates the carbonyl group to produce the first compound.

8. The method as claimed in claim 1 , wherein the substrate compound is a cyclic thiocarbamate, a chain thiocarbamate, a cyclic thiocarbonate, a chain thiocarbonate, a cyclic thiourea or a chain thiourea, the atomic group containing CX is a thiocarbonyl group, and the reaction of the substrate compound with an alkylenediamine as the second compound eliminates the thiocarbonyl group to produce the first compound.

9. The method as claimed in claim 7 wherein the alkylenediamine is ethylenediamine.

10. The method as claimed in claim 1 , wherein the reaction is carried out in the absence of solvent.

11. The method as claimed in claim 1 , wherein the reaction is carried out under microwave irradiation.

12. The method as claimed in claim 1 , wherein the first compound has an amino group.

13. The method as claimed in claim 12 , wherein the first compound also has a hydroxyl group.

14. A method, for producing a first compound having at least one of an amino group and a hydroxyl group from a substrate compound having an atomic group containing a carbonyl or thiocarbonyl group CX, wherein X represents an oxygen atom or a sulfur atom, the method comprising allowing said substrate compound to react with a second compound in the presence of an ammonium salt at a temperature of 120° C. or lower to eliminate said atomic group containing the CX from said substrate compound,
wherein the second compound is selected from:

Assignees

• Ohshima Takashi
• Morimoto Hiroyuki
• Shimizu Yuhei
• Univ Kyushu Nat Univ Corp

Inventors

• Ohshima Takashi
• Morimoto Hiroyuki
• Shimizu Yuhei

Classifications

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07B41/02

  of hydroxy or O-metal groups · CPC title

• C07D309/12

  only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers · CPC title

• C07C29/00

  Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring · CPC title

• C07C227/06

  by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid · CPC title