CN1053180C - N-(beta-aminoethyl) aniline compounds, prepn. method thereof - Google Patents
N-(beta-aminoethyl) aniline compounds, prepn. method thereof Download PDFInfo
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- CN1053180C CN1053180C CN95104262A CN95104262A CN1053180C CN 1053180 C CN1053180 C CN 1053180C CN 95104262 A CN95104262 A CN 95104262A CN 95104262 A CN95104262 A CN 95104262A CN 1053180 C CN1053180 C CN 1053180C
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Abstract
The present invention relates to a novel method for preparing a compound with the structure disclosed in the specification. In the formula, R1 represents hydrogen atoms, methyl, ethyl, propyl or butyl, and R2 represents hydrogen atoms, methyl, ethyl, methoxyl, ethoxyl or halogen atoms. The preparing method comprises: aniline and alkylamine halide react in the presence of water and inorganic anhydride. The method of the present invention can reduce the product cost and enhance the yield. The compound is a novel Trinder's reaction color radical used in clinical biochemical tests and can also be used as a coloring agent and a level dyeing agent in dye industry and an intermediate body in pharmaceutical industry.
Description
The present invention is a kind of about having in the presence of the mineral alkali, by the improvement technology of phenyl amines and haloalkyl amine prepared in reaction N-(beta-aminoethyl) amino benzenes compounds.
At present, in the clinical biochemical check, use various types of novel Trinder ' s to react look group more and more widely, to substitute such as old colour developing groups such as phenol.Have good water solubility because of these novel Trinder ' s react look group, highly sensitive, colour stable also can suppress advantages such as bilirubin and xitix interference.Be subjected to very much the welcome on clinical biochemical check circle, exploitation, application prospect are preferably arranged.N-(beta-aminoethyl) amino benzenes compounds is novel Trinder ' the s reaction of class look group just.In addition, this compounds is widely used as tinting material and levelling agent in dyestuffs industries, and is the intermediate in the medicine industry.
In the preparation of in the past N-(beta-aminoethyl) amino benzenes compounds, (as: R.L.Bent.etc, J.Am.chem.soc.733123, nineteen fifty-one), generally will drop into double above molar organic amine, wherein half participated in reaction as raw material, and second half participates in reaction as alkali, in reaction, only play acid binding agent, thus, cause the waste of raw material.And the preparation of raw material organic amine will be passed through many steps such as Reaction Separation, purification, and difficulty is big, causes the yield of product low, the cost height.According to the existing problem of technology in the past, the purpose of this invention is to provide a kind of new preparation method.The method that the present invention adopts mineral alkali to replace half organic amine to react has reduced cost, has improved yield.(on average improving about yield 10-30%).
The prepared compound of method provided by the invention has structure shown in (I) formula:
R in the formula
1Represent hydrogen atom, or methyl, ethyl, propyl group, butyl; R
2Represent hydrogen atom, methyl, ethyl, methoxyl group, oxyethyl group, halogen atom.
Described method is characterised in that:
With formula (II) compound and formula (II) compound
Under water and mineral alkali existence condition, condensation reaction takes place.X represents halogen atom.
Feature of the present invention is that also used mineral alkali is CaCO in the reaction
3, Na
2CO
3, K
2CO
3, wherein first-selected reagent is CaCO
3And compound in reaction (II) is 1: 0.1～2mol with the ratio of mineral alkali; Compound (II) is 1: 0.5～3mol with the ratio of compound (III); Halogen atom in the compound (II) comprises bromine, chlorine, iodine.In addition, the temperature of reaction during feature of the present invention also is to react is 80～180 ℃; Reaction times is 1～10 hour.
Preparation method provided by the invention can describe in detail by embodiment.
Embodiment 1:
The preparation of N-methyl-N-(beta-aminoethyl) meta-aminotoluene
With N-methyl meta-aminotoluene 9.2g (0.076mol) and 2-bromine ethylamine hydrogen bromide salt 23g (0.11mol), Ca-CO
37.6g (0.076mol), H
2O56ml, under in a three-necked bottle, mixing, stirring, about 145 ℃ reactions of holding temperature 2-4 hour, stopped reaction, mixture furnishing alkalescence, use ether extraction, use the NaOH drying, after concentrating, underpressure distillation, collect 114-116 °/10mmHg fraction, must measure 8.8g, yield 70.57% (pressing N-methyl meta-aminotoluene calculates).
Embodiment 2:
The preparation of N-ethyl-N-(beta-aminoethyl) meta-aminotoluene
Experimental installation, operation is with embodiment 1.
Raw material feed ratio: N-ethyl-m-toluidine 25g (0.19mol), 2-bromine ethylamine hydrogen bromide salt 60g (0.29mol), Ca
2CO
310g (0.1mol), H
2O15ml.112-114 °/8mmHg fraction is collected in underpressure distillation.Must measure 16.8g, yield 51%.
Embodiment 3:
The preparation of N-ethyl-N-(beta-aminoethyl) aniline
Experimental installation, operation is with embodiment 1.
Raw material feed ratio: N-ethylaniline 19.7g (0.16mol), 2-bromine ethylamine hydrogen bromide salt 49.2g (0.24mol), CaCO
38g (0.08mol), H
2O12ml.110-114 °/10mmHg fraction is collected in underpressure distillation.Must measure 15g, yield 56.2%.
Claims (8)
1. be prepared as follows the method for N-(beta-aminoethyl) amino benzenes compounds shown in the formula (I):
R wherein
1Represent hydrogen atom or methyl, ethyl, propyl group, butyl, R
2Represent hydrogen atom, methyl, ethyl, methoxyl group, oxyethyl group, halogen atom.
Described method is characterized in that:
With formula (II) compound and formula (III) compound
React under water and mineral alkali existence condition, wherein X represents halogen atom.
2. according to the method for claim 1, it is characterized in that used mineral alkali is CaCO in the reaction
3, Na
2CO
3Or K
2CO
3
3. according to the method for claim 1, it is characterized in that used mineral alkali is CaCO in the reaction
3
4. according to the method for claim 1, compound (II) is 1: 0.1～2mol with the ratio of mineral alkali in it is characterized in that reacting.
5. according to the method for claim 1, compound (II) is 1: 0.5～3mol with the ratio of compound (III) in it is characterized in that reacting.
6. according to the method for claim 1, it is characterized in that the halogen in the compound (III) comprises bromine, chlorine, iodine atom in the reaction.
7. according to the method for claim 1, the temperature of reaction in it is characterized in that reacting is 80 ℃～180 ℃.
8. according to the method for claim 1, the reaction times during its feature also is to react is 1-10 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95104262A CN1053180C (en) | 1995-05-08 | 1995-05-08 | N-(beta-aminoethyl) aniline compounds, prepn. method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95104262A CN1053180C (en) | 1995-05-08 | 1995-05-08 | N-(beta-aminoethyl) aniline compounds, prepn. method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1117486A CN1117486A (en) | 1996-02-28 |
| CN1053180C true CN1053180C (en) | 2000-06-07 |
Family
ID=5075060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95104262A Expired - Fee Related CN1053180C (en) | 1995-05-08 | 1995-05-08 | N-(beta-aminoethyl) aniline compounds, prepn. method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1053180C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112679366A (en) * | 2020-12-14 | 2021-04-20 | 上海俪源科技有限公司 | Purification method of N- (2-aminoethyl) -N-ethyl m-toluidine |
| CN112552187A (en) * | 2020-12-14 | 2021-03-26 | 上海俪源科技有限公司 | Purification method of N- (2-aminoethyl) -N-ethyl m-toluidine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86107268A (en) * | 1986-10-23 | 1988-05-04 | 尤尼罗亚尔化学公司 | The preparation method of the single substituted p-phenylenediamine compounds of N- |
| EP0497133A1 (en) * | 1991-01-26 | 1992-08-05 | Bayer Ag | Process for the preparation of (hetero)arylalk(en/in)-ylamines and (hetero)arylalkinylamines per se |
-
1995
- 1995-05-08 CN CN95104262A patent/CN1053180C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86107268A (en) * | 1986-10-23 | 1988-05-04 | 尤尼罗亚尔化学公司 | The preparation method of the single substituted p-phenylenediamine compounds of N- |
| EP0497133A1 (en) * | 1991-01-26 | 1992-08-05 | Bayer Ag | Process for the preparation of (hetero)arylalk(en/in)-ylamines and (hetero)arylalkinylamines per se |
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| Publication number | Publication date |
|---|---|
| CN1117486A (en) | 1996-02-28 |
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