CN1849300A - Method for producing N,N -dialkoxy-N,N -dialkyl oxamide - Google Patents
Method for producing N,N -dialkoxy-N,N -dialkyl oxamide Download PDFInfo
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Abstract
The present invention provides a process for preparing an N,N'-dialkoxy-N,N'-dialkyl oxamide represented by the formula (3) : wherein R 2 and R 3 may be the same or different from each other, and each represent an alkyl group having 1 to 4 carbon atoms, which comprises reacting an oxalic acid diester represented by the formula (1): wherein R 1 and R 1' may be the same or different from each other, and each represent a hydrocarbon group, and an N-alkyl-O-alkylhydroxylamine represented by the formula (2): R 2 O-NHR 3 (2) wherein R 2 and R 3 have the same meanings as defined above, or an acid salt thereof in the presence of a base.
Description
Technical field
The present invention relates to the useful N of synthetic intermediate, N '-dialkoxy-N, the novel preparation method of N '-dialkyl group oxamide as medicine, agricultural chemicals etc.
Bei Jing Ji Intraoperative
In the past, as N, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide, disclose in the presence of pyridine, made oxalyl chloride and N, N is prepared in the reaction of O-dimethyl hydroxyl amine hydrochlorate, N '-dimethoxy-N, the method for N '-dimethyl oxamide is (for example with reference to J.Org.Chem.
60, 5016 (1995)).But, in the method, as the initial feed use is the oxalyl chloride that is decomposed into high phosgene of toxicity and carbon monoxide easily, thereby be present in the problem that to use the high methylene dichloride of carinogenicity in the lock out operation of object, and as N, N '-dialkoxy-N, the industrial production process of N '-dialkyl group oxamide is inappropriate.
Summary of the invention
The bright problem of this development is in order to address the above problem a little, provide a kind of by initial feed safe in utilization, do not need complicated operations, just can prepare N with high yield, N '-dialkoxy-N, the suitable industrialized N of N '-dialkyl group oxamide, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide.
The present invention relates to a kind ofly in the presence of alkali, make general formula (1):
In the formula: R
1And R
1 'Can be identical also can be different, represent respectively hydrocarbon, shown in oxalate diester and general formula (2):
R
2O-NHR
3 (2)
In the formula: R
2And R
3Can be identical also can be different, represent respectively carbonatoms be 1～4 alkyl,
Shown N-alkyl-O-alkyl hydroxy amine or the reaction of its hydrochlorate generate general formula (3):
In the formula: R
2And R
3With above-mentioned same meaning,
Shown N, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide.
Embodiment
The oxalate diester that uses in the reaction of the present invention is shown in above-mentioned general formula (1).R in this general formula (1)
1And R
1 'Can be identical also can be different, be respectively hydrocarbon, for example can enumerate carbonatomss such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group and be 1～8 alkyl; Cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; Aromatic alkyl such as benzyl, styroyl; Aryl such as phenyl, tolyl, naphthyl.Wherein preferable methyl, ethyl, sec.-propyl, butyl, phenyl.In addition, these groups also comprise various isomer.
The N-alkyl that uses in reaction of the present invention-O-alkyl hydroxy amine is shown in above-mentioned general formula (2).In this general formula (2), R
2And R
3Can be the same or different, represent the alkyl of carbonatoms 1～4 respectively, for example can enumerate methyl, ethyl, propyl group, butyl.In addition, these groups also comprise various isomer.In addition, this N-alkyl-O-alkyl hydroxy amine, both can use free N-alkyl-O-alkyl hydroxy amine (also comprising hydrate), and also can be used as acid-salts such as hydrochloride, vitriol, nitrate, phosphoric acid salt and use, perhaps also can use in the mode of its aqueous solution.In addition, these N-alkyl-O-alkyl hydroxy amine can be used alone or mixed use of two or more.
The usage quantity of above-mentioned N-alkyl-O-alkyl hydroxy amine or its hydrochlorate is preferably 0.5～5.0 mole with respect to 1 mole of oxalate diester, more preferably 1.5～3.0 moles.
As the alkali that uses in the reaction of the present invention, for example can enumerate alkali metal alkoxide (also comprising corresponding alcoholic solution) such as lithium methoxide, sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, potassium tert.-butoxide; Alkali metal hydroxide such as sodium hydroxide, potassium hydroxide; Alkaline carbonates such as Quilonum Retard, yellow soda ash, salt of wormwood; Alkali metal hydrocarbonate such as sodium bicarbonate, saleratus; Amine such as triethylamine, Tributylamine, but preferred use alkali metal alkoxide, more preferably use sodium methylate, sodium ethylate.In addition, these alkali can be used alone or mixed use of two or more.
The usage quantity of above-mentioned alkali with respect to 1 mole of oxalate diester, is preferably 0.5～10 mole, more preferably 1.5～6 moles.
Reaction of the present invention is preferably carried out in solvent.As the solvent that uses, only otherwise hindering reaction then is not particularly limited, for example can enumerate alcohols such as methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol, the trimethyl carbinol; Nitrile such as acetonitrile, propionitrile; Aliphatic hydrocarbon such as hexane, heptane; Halogenated aliphatic hydrocarbon such as methylene dichloride, chloroform, tetracol phenixin; Benzene,toluene,xylene, sym-trimethylbenzene etc. are aromatic hydrocarbon based; Halogenated aromatic hydro carbons such as chlorinated benzene; Ethers such as diethyl ether, tetrahydrofuran (THF), diisopropyl ether, dioxane; N, amidess such as dinethylformamide, N,N-dimethylacetamide; Carboxylic acid esters such as vinyl acetic monomer, N-BUTYL ACETATE, ethyl propionate; Sulfoxide classes such as dimethyl sulfoxide (DMSO); Carbonic diester such as methylcarbonate, diethyl carbonate class, preferred alcohols, nitrile, aromatic hydrocarbon based, more preferably methyl alcohol, ethanol, Virahol.In addition, these solvents can be used alone or mixed use of two or more.
The usage quantity of described solvent can suit to regulate according to the homogeneity of reaction solution or stirring property etc., is 0.1～100g, 0.5～50g more preferably with respect to oxalate diester 1g preferably still.
Reaction of the present invention for example can be by mixing oxalate diester, N-alkyl-O-alkyl hydroxy amine or its hydrochlorate, alkali and solvent, and method such as reaction is carried out.Preferred-40～100 ℃ of the temperature of reaction of this moment, more preferably-20～50 ℃, anti-ying pressure and reaction times are not particularly limited.
As the N of gained among the present invention, N '-dialkoxy-N, N '-dialkyl group oxamide for example can enumerate R
2And R
3Identical or different, represent the compound of carbonatoms 1～4 alkyl respectively.
In addition, as the N of end product, N '-dialkoxy-N, N '-dialkyl group oxamide after for example can finishing by reaction, filters, concentrates, general methods such as distillation, recrystallization, column chromatography chromatogram carry out separation and purification.
The N of gained among the present invention, N '-dialkoxy-N, N '-dialkyl group oxamide, for example can prepare useful medicine or agricultural chemicals by the method for record among the special table of Japanese communique 2002-541104, special table 2004-509059 or Bioorg.Med.Chem.Lett.12 (2002) pp.3001-3004 etc.
Below, by embodiment the present invention is specifically described, but scope of the present invention is not subjected to the restriction of these embodiment.
Embodiment
Embodiment 1 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 1000ml that has whipping appts, thermometer and dropping funnel, add 98 quality % oxalic acid diethyl ester 126.8g (0.85mol), 98.1 quality %N, after O-dimethyl hydroxyl amine hydrochlorate 169.0g (1.70mol) and the methyl alcohol 100ml, in 5～10 ℃ of maintenance liquid temperature, the 28 quality % methanol solution of sodium methylate 656.0g (3.40mol) that slowly drip make it react 3 hours under this temperature while stirring.After reaction finishes, in the flask of the internal volume 2000ml that has whipping appts, thermometer and dropping funnel, add acetic acid 107.1g (1.79mol) and water 893g, be cooled to after 5 ℃, the limit keeps 5～15 ℃ of liquid temperature, and above-mentioned reaction solution and stirring slowly drips on the limit.Then, under reduced pressure concentration of reaction solution extracts with vinyl acetic monomer 1500ml then.Gained organic layer (vinyl acetic monomer layer) is concentrating under reduced pressure once more, adds normal heptane 240g then, in 5～10 ℃ of maintenance liquid temperature, stirs 30 minutes.The crystallization of separating out is filtered, and cleans the back drying under reduced pressure with the refrigerative normal heptane, obtains N as white crystals, N '-dimethoxy-N, N '-dimethyl oxamide 92.3g separation yield: 61.6%).
In addition, N, N '-dimethoxy-N, the physics value of N '-dimethyl oxamide is as follows.
Fusing point: 89.5～92.0 ℃
1H-NMR(CDCl
3，δ(ppm))；3.24(6H，s)、3.74(6H，s)
Embodiment 2 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 25ml that has whipping appts, thermometer and dropping funnel, add 99 quality % dimethyl oxalate 1.01g (8.47mmol), 98.1 quality %N, after O-dimethyl hydroxyl amine hydrochlorate 1.68g (16.94mmol) and the methyl alcohol 1ml, the limit keeps 5～10 ℃ of limits of liquid temperature, the 28 quality % methanol solution of sodium methylate 6.54g (33.88mmol) that slowly drip, and it was reacted 3 hours under this temperature.After reaction finishes, in the flask of the internal volume 25ml that has whipping appts, thermometer and dropping funnel, add after 2mol/l jealous woman acid 10ml (2.00mmol) is cooled to 5 ℃, the limit keeps slowly drip above-mentioned reaction solution and stirring of 5～15 ℃ of limits of liquid temperature.By this solution of high-efficient liquid phase chromatogram technique analysis (absolute quantitation method), the result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.21g (reaction yield: 80.9%).
Embodiment 3 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except 99 quality % dimethyl oxalate 1.01g (8.47mmol) among the embodiment 2 are replaced with 98 quality % oxalic acid diethyl ester 1.26g (8.47mmol), methyl alcohol is replaced with outside the ethanol, remaining reacts by the mode identical with embodiment 2.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.29g (reaction yield: 86.4%).
Embodiment 4 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except 99 quality % dimethyl oxalate 1.01g (8.47mmol) among the embodiment 2 are replaced with 99 quality % oxalic acid diisopropyl ester 1.49g (8.47mmol), methyl alcohol is replaced with the ethanol, remaining reacts by mode similarly to Example 2.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.23g (reaction yield: 82.4%).
Embodiment 5 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except 99 quality % dimethyl oxalate 1.01g (8.47mmol) among the embodiment 2 are replaced with 99 quality % dibutyl oxalate 1.73g (8.47mmol), methyl alcohol is replaced with the ethanol, remaining reacts by mode similarly to Example 2.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.24g (reaction yield: 83.1%).
Embodiment 6 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except 99 quality % dimethyl oxalate 1.01g (8.47mmol) among the embodiment 2 are replaced with 99 quality % phenyloxalate 2.07g (8.47mmol), methyl alcohol is replaced with the ethanol, remaining reacts by mode similarly to Example 2.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 0.85g (reaction yield: 57.1%).
Embodiment 7 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the Virahol, remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.21g (reaction yield: 80.8%).
Embodiment 8 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the acetonitrile, remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, and N '-dimethyl oxamide 1.18g generates (reaction yield: 78.8%).
Embodiment 9 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the methylcarbonate, remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, and N '-dimethyl oxamide 1.13g generates (reaction yield: 75.7%).
Embodiment 10 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the dimethyl formamide, remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.16g (reaction yield: 77.5%).
Embodiment 11 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the tetrahydrofuran (THF), remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.25g (reaction yield: 83.6%).
Embodiment 12 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
Except the ethanol among the embodiment 3 is replaced with the toluene, remaining reacts by mode similarly to Example 3.Its result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 1.05g (reaction yield: 71.0%).
Embodiment 13 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 25ml that has whipping appts and thermometer, add 99 quality % dimethyl oxalate 1.01g (8.47mmol), 98.1 quality %N, after O-dimethyl hydroxyl amine hydrochlorate 1.68g (16.94mmol) and the dimethyl sulfoxide (DMSO) 5ml, in 5～25 ℃ of maintenance liquid temperature, divide to add 95 quality % sodium methylate powder 1.93g (33.88mmol) for several times, it was reacted 1.5 hours under this temperature.After reaction finishes, in the flask of the internal volume 25ml that has whipping appts, thermometer and dropping funnel, add after 2mol/l acetic acid 10ml (2.00mmol) is cooled to 5 ℃, the limit keeps slowly drip above-mentioned reaction solution and stirring of 5～15 ℃ of limits of liquid temperature.By this solution of high-efficient liquid phase chromatogram technique analysis (absolute quantitation method), the result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 0.91g (reaction yield: 61.0%).
Embodiment 14 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 200ml that has whipping appts, thermometer and dropping funnel, add 98 quality % oxalic acid diethyl ester 12.63g (84.7mmol), 98.8 quality %N, behind O-dimethyl hydroxyl amine hydrochlorate 16.72g (169.4mmol) and the methyl alcohol 10ml, the limit keeps 3～7 ℃ of liquid temperature, the limit 28 quality % methanol solution of sodium methylate 65.36g (338.8mmol) that slowly drip make it 3～8 ℃ of reactions 3 hours while stirring.After reaction finished, in the flask of the internal volume 300ml that has whipping appts, thermometer and dropping funnel, after adding 2mol/l hydrochloric acid 90ml (180mmol) and cooling off 5 ℃, the limit kept slowly drip above-mentioned reaction solution and stirring of 5～15 ℃ of limits of liquid temperature.By this solution of high-efficient liquid phase chromatogram technique analysis (absolute quantitation method), the result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 13.25g (reaction yield: 88.8%).
Embodiment 15 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 200ml that has whipping appts, thermometer and dropping funnel, add 98 quality % oxalic acid diethyl ester 12.63g (84.7mmol), 98.8 quality %N, behind O-dimethyl hydroxyl amine hydrochlorate 16.72g (169.4mmol) and the methyl alcohol 10ml, the 28 quality % methanol solution of sodium methylate 65.36g (338.8mmol) that slowly drip when keeping liquid temperature-10～-7 ℃ make it-9～-7 ℃ of reactions 3 hours while stirring.After reaction finishes, in the flask of the internal volume 300ml that has whipping appts, thermometer and dropping funnel, add 2mol/l hydrochloric acid 90ml (180mmol), be cooled to 5 ℃ after, the limit keeps slowly drip above-mentioned reaction solution and stirring of 5～15 ℃ of limits of liquid temperature.By this solution of high-efficient liquid phase chromatogram technique analysis (absolute quantitation method), the result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 13.12g (reaction yield: 87.9%).
Embodiment 16 (N, N '-dimethoxy-N, N '-dimethyl oxamide synthetic)
In the flask of the internal volume 200ml that has whipping appts, thermometer and dropping funnel, add 98 quality % oxalic acid diethyl ester 12.63g (84.7mmol), 98.8 quality %N, behind O-dimethyl hydroxyl amine hydrochlorate 20.07g (203.3mmol) and the methyl alcohol 10ml, the limit keeps 3～7 ℃ of limits of liquid temperature, the 28 quality % methanol solution of sodium methylate 71.90g (372.7mmol) that slowly drip, and makes it 3～7 ℃ of reactions 3 hours while stirring.After reaction finishes, in the flask of the internal volume 300ml that has whipping appts, thermometer and dropping funnel, add 1.7mol/l hydrochloric acid 110ml (187mmol), be cooled to 5 ℃ after, the limit keeps slowly drip above-mentioned reaction solution and stirring of 5～15 ℃ of limits of liquid temperature.By this solution of high-efficient liquid phase chromatogram technique analysis (absolute quantitation method), the result generates N, N '-dimethoxy-N, N '-dimethyl oxamide 14.32g (reaction yield: 96.0%).
Utilize possibility on the industry
The present invention relates to as useful N of synthetic intermediate such as medicine, agricultural chemicals, N '-dialkoxy-N, N '-The novel preparation method of dialkyl group oxamides.
This development of Tong Guo is bright can to provide a kind of industrialized N of being fit to, N '-dialkoxy-N, N '-dialkyl group grass The preparation method of acid amides, the method do not need complicated operation by using safe initial feed, Just can prepare N with high yield, N '-dialkoxy-N, N '-dialkyl group oxamides.
Claims (16)
1. the N shown in the general formula (3), N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, in the presence of alkali, makes general formula (1):
In the formula: R
1And R
1 'Identical or different, represent respectively hydrocarbon,
Shown oxalate diester and general formula (2):
R
2O-NHR
3 (2)
In the formula: R
2And R
3Identical or different, represent respectively carbonatoms be 1～4 alkyl,
Shown N-alkyl-O-alkyl hydroxy amine or the reaction of its hydrochlorate,
In the formula: R
2And R
3With above-mentioned same meaning.
2. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide, it is characterized in that alkali is to be selected from least a in the material group that is made of alkali metal alkoxide, alkali metal hydroxide, alkaline carbonate, alkali metal hydrocarbonate and amine.
3. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide, it is characterized in that alkali is to be selected from least a in the material group that is made of lithium methoxide, sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, potassium tert.-butoxide, sodium hydroxide, potassium hydroxide, Quilonum Retard, yellow soda ash, salt of wormwood, sodium bicarbonate, saleratus, triethylamine and Tributylamine.
4. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, alkali is to be selected from least a in the material group that is made of sodium methylate and sodium ethylate.
5. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the usage quantity of alkali is to be 0.5～10 mole with respect to 1 mole of oxalate diester.
6. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the usage quantity of alkali is to be 1.5～6 moles with respect to 1 mole of oxalate diester.
7. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, reaction is to carry out in solvent.
8. N according to claim 3, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide, it is characterized in that solvent is to be selected from least a in the material group that is made of alcohols, nitrile, aliphatic hydrocarbon, halogenated aliphatic hydrocarbon, aromatic hydrocarbon based, halogenated aromatic hydro carbons, ethers, amides, carboxylic acid esters, sulfoxide class and carbonic diester class.
9. N according to claim 3, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide, it is characterized in that, solvent is to be selected from by methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol, the trimethyl carbinol, acetonitrile, propionitrile, hexane, heptane, methylene dichloride, chloroform, tetracol phenixin, benzene, toluene, dimethylbenzene, sym-trimethylbenzene, chlorinated benzene, diethyl ether, tetrahydrofuran (THF), diisopropyl ether, dioxane, N, dinethylformamide, N,N-dimethylacetamide, vinyl acetic monomer, N-BUTYL ACETATE, ethyl propionate, dimethyl sulfoxide (DMSO), at least a in the material group that methylcarbonate and diethyl carbonate constitute.
10. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the usage quantity of solvent is to be 0.1～100g with respect to the 1g oxalate diester.
11. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the usage quantity of solvent is to be 0.5～50g with respect to the 1g oxalate diester.
12. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the R in the oxalate diester shown in the formula (1)
1And R
1 'Be to be selected from least a in the material group that constitutes by alkyl, cycloalkyl, aromatic alkyl and aryl.
13. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the R in the oxalate diester shown in the formula (1)
1And R
1 'Be be selected from the material group that constitutes by methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzyl, styroyl, phenyl, tolyl and naphthyl at least a.
14. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the R in the N-alkyl shown in the formula (2)-O-alkyl hydroxy amine
2And R
3Be respectively to be selected from least a in the material group that constitutes by methyl, ethyl, propyl group and butyl.
15. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the N-alkyl-O-alkyl hydroxy amine shown in the formula (2) or the usage quantity of its hydrochlorate are 0.5～5.0 mole for 1 mole with respect to the oxalate diester shown in the formula (1).
16. N according to claim 1, N '-dialkoxy-N, the preparation method of N '-dialkyl group oxamide is characterized in that, the N-alkyl-O-alkyl hydroxy amine shown in the formula (2) or the usage quantity of its hydrochlorate are 1.5～3.0 moles for 1 mole with respect to the oxalate diester shown in the formula (1).
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|---|---|---|---|
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