JP2001233851A - N-(2-hydroxyethyl)-2-arylsulfonylethylamine and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new N-(2-hydroxyethyl)-2-arylsulfonylethylamine expressed by the general formula (2) [R1 and R2 may be the same to or different from each other, and are each H, a halogen, a lower alkyl, a lower alkoxyl, nitro, amino, a lower alkylamino or a di(lower alkyl)amino]. SOLUTION: This method of producing the N-(2-hydroxyethyl)-2- arylsulfonylethylamine comprises reacting an aryl vinyl sulfone expressed by the general formula (1) with monoethanolamine.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to N- (2-hydroxyethyl) -2-arylsulfonylethylamine and a method for producing the same.

[0002]

2. Description of the Related Art N- (2-hydroxyethyl) -2-arylsulfonylethylamine can be derived, for example, as an antitumor agent having a naphthalimide skeleton and is considered to be an important compound as a pharmaceutical intermediate. The production example of the compound was not known.

[0003]

DISCLOSURE OF THE INVENTION The present inventors have found a method for producing a novel compound, N- (2-hydroxyethyl) -2-arylsulfonylethylamine, and have accomplished the present invention.

[0004]

That is, the present invention provides a compound represented by the following general formula (1): (Wherein, R ¹ and R ² are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, a lower alkylamino group or a di (lower alkyl) amino group. N- (2-hydroxyethyl) -2-arylsulfonylethylamine represented by the formula: and a method for producing the same.

[0005]

DETAILED DESCRIPTION OF THE INVENTION General formula (1) The substituents R ¹ and R ² of N- (2-hydroxyethyl) -2-arylsulfonylethylamine represented by
Represents a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, a lower alkylamino group or a di (lower alkyl) amino group.

A halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and a lower alkyl group is, for example, a methyl group, an ethyl group, an n-propyl group,
A linear or branched alkyl group having 1 to 6 carbon atoms such as an n-butyl group, an n-pentyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and a neopentyl group is a lower alkoxy group. For example, methoxy, ethoxy, n-propoxy, n-butoxy,
Examples thereof include a linear or branched alkoxy group having 1 to 6 carbon atoms such as an n-pentoxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and a neopentoxy group.

The lower alkylamino group is an amino group substituted with one lower alkyl group, and examples of the lower alkyl group are the same as those described above. Specific examples of such a lower alkylamino group include a methylamino group, an ethylamino group, a tert-butylamino group, and the like. The di (lower alkyl) amino group is exemplified by an amino group in which two lower alkyl groups are substituted as described above, and the two lower alkyl groups may be the same or different. Specific examples of such a di (lower alkyl) amino group include a dimethylamino group, a methylethylamino group, a diethylamino group, and a tert-butylmethylamino group.

Specific examples of N- (2-hydroxyethyl) -2-arylsulfonylethylamine represented by the general formula (1) include, for example, N- (2-hydroxyethyl) -2-phenylsulfonylethylamine and N- (2-hydroxyethyl) -2-phenylsulfonylethylamine. (2
-Hydroxyethyl) -2- (4-chlorosulfonylphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (3,4-dichlorophenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2
-(4-bromophenylsulfonyl) ethylamine, N
-(2-hydroxyethyl) -2- (4-iodophenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (4-methylphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (2,4
-Dimethylphenylsulfonyl) ethylamine, N-
(2-hydroxyethyl) -2- (4-ethylphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (4-isopropylphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- ( 4
-Tert-butylphenylsulfonyl) ethylamine,

N- (2-hydroxyethyl) -2- (4
-Methoxyphenylsulfonyl) ethylamine, N-
(2-hydroxyethyl) -2- (3,4-dimethoxyphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (4-t-butoxyphenylsulfonyl) ethylamine, N- (2-hydroxyethyl) −
2- (3-aminophenylsulfonyl) ethylamine,
N- (2-hydroxyethyl) -2- (3-methylaminophenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (3-ethylaminophenylsulfonyl) ethylamine, N- (2-hydroxyethyl)
-2- (3-dimethylaminophenylsulfonyl) ethylamine, N- (2-hydroxyethyl) -2- (3-
Diethylaminophenylsulfonyl) ethylamine, N
-(2-hydroxyethyl) -2- (3-nitrophenylsulfonyl) ethylamine and the like.

The N- (2-hydroxyethyl)-of the present invention
2-arylsulfonylethylamine is represented by the general formula (2) (Wherein, R ¹ and R ² have the same meanings as described above), and can be produced by reacting monovinylamine with monoarylamine. Here, as the substituents R ¹ and R ² in the general formula (2), the same substituents as described above can be exemplified.

The aryl vinyl sulfone represented by the general formula (2) is obtained, for example, by reacting thiophenol with 1,2-dihaloethane and then oxidizing the same.
A method of treating a haloethylaryl sulfone with a base (O
rg. Synth. , 64 , 157 (1985);
Org. Chem. , 58 , 4506 (1993)),
A method in which thiophenol is reacted with 2-chloroethanol, chlorinated, and further oxidized to give a base treatment of 2-chloroethylarylsulfone (J. Che.
m. Soc. , 1754 (1949)), a method of treating a sulfate of 2-arylsulfonylethanol with a base (German Patent No. 842198 (1942)) or a method of treating a methanesulfonate of 2-arylsulfonylethanol with a base (Bull. Korea).
n Chem. Soc. , 16 , 670 (1995))
Etc., and the production method is not particularly limited.

Specific examples of such aryl vinyl sulfones include, for example, phenyl vinyl sulfone, 4-chlorophenyl vinyl sulfone, 3,4-dichlorophenyl vinyl sulfone, 4-bromophenyl vinyl sulfone,
-Iodophenylvinylsulfone, 4-methylphenylvinylsulfone, 2,4-dimethylphenylvinylsulfone, 4-ethylphenylvinylsulfone, 4-isopropylphenylvinylsulfone, 4-tert-butylphenylvinylsulfone, 4-methoxyphenylvinyl Sulfone, 3,4-dimethoxyphenylvinylsulfone, 4-t-butoxyphenylvinylsulfone, 3-aminophenylvinylsulfone, 3-methylaminophenylvinylsulfone, 3-ethylaminophenylvinylsulfone, 3-dimethylaminophenylvinylsulfone ,
3-diethylaminophenylvinylsulfone, 3-nitrophenylvinylsulfone and the like.

In the reaction of aryl vinyl sulfone with monoethanolamine, the amount of monoethanolamine used is usually 0.5 to 0.5
It is in the range of 5 mole times, preferably 0.8 to 3 mole times.

The reaction may be carried out without a solvent or in a solvent. When the reaction is carried out in a solvent, examples of the solvent include ether solvents such as dimethoxyethane, tetrahydrofuran, and ethyl ether; aromatic solvents such as benzene, toluene, xylene, chlorobenzene, and dichlorobenzene; and aliphatic hydrocarbons such as hexane and heptane. Hydrogen solvent, aliphatic halogenated hydrocarbon solvent such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, etc., aprotic polar solvent such as N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile, ethyl acetate, butyl acetate And the like, or a solvent inert to the reaction such as water, alone or in a mixture, and the amount of the solvent is not particularly limited.

The reaction is usually carried out at a temperature in the range from -30 ° C. to the reflux temperature of the reaction mixture. When a solvent is used, the temperature is preferably not higher than the boiling point of the solvent.

After completion of the reaction, the desired N- (2-hydroxyethyl) -2-arylsulfonylethylamine can be obtained by, for example, concentrating the reaction mixture. The N- (2-hydroxyethyl) -2-arylsulfonylethylamine thus obtained may be further purified by a method such as column chromatography.

Thus, N- (2) represented by the general formula (1)
-Hydroxyethyl) -2-arylsulfonylethylamine can be obtained.

[0018]

According to the present invention, a novel N- (2-hydroxyethyl) -2-arylsulfonylethylamine can be produced.

[0019]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 5.07 g of phenyl vinyl sulfone was added to 30 m of ethyl acetate.
Then, 3.70 g of monoethanolamine was added, and the mixture was stirred at room temperature (20 ° C.) for 10 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain 8.91 g of a pale yellow oil containing N- (2-hydroxyethyl) -2-phenylsulfonylethylamine. GC-MS spectrum:
230 (M ⁺ ), 228, 211, 198, 186, 1
69, 141, 125, 120, 105, 91, 77,
66,56,44,28

Claims (2)

[Claims] 1. The general formula (1) (Wherein, R ¹ and R ² are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, a lower alkylamino group or a di (lower alkyl) amino group. N- (2-hydroxyethyl) -2-arylsulfonylethylamine represented by the following formula: 2. The general formula (2) (Wherein, R ¹ and R ² each have the same meaning as described above), wherein N- (2-hydroxyethyl) -2-arylsulfonyl is reacted with arylvinylsulfone and monoethanolamine. A method for producing ethylamine.