CN103319424A - Synthesis method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one - Google Patents
Synthesis method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one Download PDFInfo
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- CN103319424A CN103319424A CN2013102754738A CN201310275473A CN103319424A CN 103319424 A CN103319424 A CN 103319424A CN 2013102754738 A CN2013102754738 A CN 2013102754738A CN 201310275473 A CN201310275473 A CN 201310275473A CN 103319424 A CN103319424 A CN 103319424A
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- triazine
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- ketone
- tertiary butyl
- sulfydryl
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- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000001308 synthesis method Methods 0.000 title abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 64
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 22
- 238000001035 drying Methods 0.000 claims abstract description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 20
- 238000009413 insulation Methods 0.000 claims description 16
- 235000007715 potassium iodide Nutrition 0.000 claims description 15
- 229960004839 potassium iodide Drugs 0.000 claims description 15
- 238000010189 synthetic method Methods 0.000 claims description 14
- 238000013019 agitation Methods 0.000 claims description 9
- 238000001291 vacuum drying Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000004904 shortening Methods 0.000 abstract 1
- 238000010812 external standard method Methods 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- 241000230452 Cyclothone braueri Species 0.000 description 1
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a synthesis method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one, which comprises the following steps: by using acetone as solvent and potassium iodide as a catalyst, reacting 4-amino-6-tert-butyl-3-thio-1,2,4-triazine-5(4H)-one, dimethyl sulfate and anhydrous sodium carbonate according to a mol ratio of 1:(1.05-1.5):(1.5-2) while keeping the temperature at 15-45 DEG C for 2-5 hours; and finally, recovering the acetone, adding water to perform precipitation, separating, and drying to obtain the 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one. The raw materials used in the method disclosed by the invention are accessible and low in cost; the method disclosed by the invention is mild in reaction, and the reaction parameters are easy to control, thus ensuring the safety of the production process; the potassium iodide is used as the catalyst, so that the reaction can be quickly and completely performed at normal temperature, thus greatly shortening the production cycle and effectively lowering the production cost; the yield of the product is high and is up to 90% or above; and the product with a content of 96% or above can be directly obtained. Thus, the invention conforms to requirements of industrial production, and has better application prospects.
Description
Technical field
The present invention relates to the synthesis technical field of Triazinone weedicide, specifically, is a kind of 4-amino-6-tertiary butyl-3-methylthio group-1,2, the synthetic method of 4-triazine-5 (4H)-ketone.
Background technology
4-amino-6-the tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone, commodity are called the piperazine humulone, claim again sencorex, Garrick to remove molecular formula: C
8H
14N
4OS, molecular weight: 214.28.It is a kind of interior suction selective herbicide, and mainly by root absorption, stem, leaf also can absorb, and annual broadleaf weed and part gramineous weeds are had good preventive effect, is that one of maximum weedicide kind is used in the whole world at present.The present 4-amino-6-tertiary butyl-3-methylthio group-1,2, the manufacturer of 4-triazine-5 (4H)-ketone is numerous, the synthetic main following dual mode that adopts of its finished product:
One, monobromethane method, its reaction equation is:
；
Two, methyl alcohol sulfuric acid process, its reaction equation is:
。
The first monobromethane method is mainly used monobromethane, and this raw material is gas at normal temperatures and pressures, is generally steel cylinder and stores, and the buying transportation is very inconvenient, and expensive, toxicity is larger, and reaction needs pressurization, high to equipment requirements, larger to leaking the strick precaution difficulty, the personnel that very easily cause poison.Because this reaction needs to carry out in absolute airtight container, therefore can't effectively control reaction end, cause being difficult to obtain higher yields and highly purified product, it enters the world market all will can reach the WHO quality standard through purifying.
The second methyl alcohol sulfuric acid process needs long-time back flow reaction, generally need 20～30 hours its transformation efficiencys can reach about 80%, production efficiency is extremely low, and quality product is relatively poor, because of through long-time pyroreaction, so that sulfydryl and the amino oxidizing reaction that occurs, cause that product impurity is more and color and luster is darker, need just to can be used as the finished product sale through purifying repeatedly.
Therefore, need that a kind of starting material are easy to get, cheap, reaction temperature and, high, the good product quality of product yield and production safety obtain the 4-amino-6-tertiary butyl-3-methylthio group-1, the solution of 2,4-triazine-5 (4H)-ketone yet there are no report about method of the present invention at present.
Summary of the invention
The objective of the invention is to be difficult for buying, expensive for starting material of the prior art, production is dangerous wayward, and quality product is relatively poor, the shortcomings such as yield is low, provide a kind of 4-amino-6-tertiary butyl-3-methylthio group-1,2, the synthetic method of 4-triazine-5 (4H)-ketone.
For achieving the above object, the technical scheme taked of the present invention is:
A kind of 4-amino-6-tertiary butyl-3-methylthio group-1,2, the synthetic method of 4-triazine-5 (4H)-ketone, it is with acetone, 4-amino-6-the tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, anhydrous sodium carbonate and potassiumiodide join in the reactor, then control 15～45 ℃ of temperature under the agitation condition and drip methyl-sulfate, after dropwising 15～45 ℃ of lower insulation reaction 2～5 hours, reclaim at last acetone, add the elutriation material, separating also, drying obtains the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, the mol ratio of methyl-sulfate and anhydrous sodium carbonate is 1:1.05～1.5:1.5～2.
Reaction equation is:
，
Wherein, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone is substrate, and methyl-sulfate is methyl donor, and acetone is made solvent, and yellow soda ash helps reagent, and potassiumiodide is made catalyzer.
The consumption of described acetone is: the every mole of 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone is with 500～600 milliliters of acetone.
The consumption of described potassiumiodide is: the every mole of 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone restrains potassiumiodide with 1～1.5.
Preferably, described temperature of reaction is 25～35 ℃.
Preferably, the described reaction times is 3～4 hours.
Described drying is 60 ℃ of vacuum-dryings.
As a kind of preferred implementation of the inventive method, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.3:1.8.
As a kind of preferred implementation of the inventive method, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.5:1.5.
As a kind of preferred implementation of the inventive method, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.4:1.6.
As a kind of preferred implementation of the inventive method, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.2:1.7.
The advantage of the inventive method is:
The raw material of using in the inventive method is easy to get, and cheap; The inventive method reaction temperature and, reaction parameter easy to control can guarantee the security of production process; Adopt potassiumiodide to make catalyzer, so that react completely rapidly at normal temperatures, greatly reduce its production cycle, effectively reduce production cost; Product yield is high, reaches more than 90%, can directly obtain content at the product more than 96%, meets industrialization production requirements, has the prospect of using preferably.
Embodiment
The below elaborates to embodiment provided by the invention.
Embodiment 1
With acetone 400mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 150g(0.75mol), anhydrous sodium carbonate 120g(1.13mol), potassiumiodide 1g joins in the 1000mL four-hole reaction flask, 25～30 ℃ of slow methyl-sulfate 102g(0.81mol that drip of control temperature under the agitation condition), dropwise, kept 25～30 ℃ of insulation reaction 2 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 600mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 145.7g(0.68mol), molar yield is 90.66%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 96.28%.HPLC external standard method testing conditions is: U.S. waters high performance liquid chromatograph, C18 chromatographic column, specification 150mm * 4.6mm; Moving phase, methyl alcohol: water=65:35(V/V), flow velocity 1.0mL/min; Column temperature is room temperature, detects wavelength 254nm, and sample size is 10 μ L.
Embodiment 2
With acetone 800mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 300g(1.5mol), anhydrous sodium carbonate 287g(2.71mol), potassiumiodide 2g joins in the 2000mL four-hole reaction flask, 30～35 ℃ of slow methyl-sulfate 245.7g(1.95mol that drip of control temperature under the agitation condition), dropwise, kept 30～35 ℃ of insulation reaction 3 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 1200mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 293.6g(1.37 mol), molar yield is 91.33%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 96.31%.HPLC external standard method testing conditions is with embodiment 1.
Embodiment 3
With acetone 800mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 300g(1.5mol), anhydrous sodium carbonate 315g(2.97mol), potassiumiodide 2g joins in the 2000mL four-hole reaction flask, 35～40 ℃ of slow methyl-sulfate 280g(2.22mol that drip of control temperature under the agitation condition), dropwise, kept 35～40 ℃ of insulation reaction 5 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 1200mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 300g(1.4 mol), molar yield is 93.45%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 97.31%.HPLC external standard method testing conditions is with embodiment 1.
Embodiment 4
With acetone 375mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 150g(0.75mol), anhydrous sodium carbonate 159g(1.5mol), potassiumiodide 0.75g joins in the 1000mL four-hole reaction flask, 15～20 ℃ of slow methyl-sulfate 99.225g(0.7875mol that drip of control temperature under the agitation condition), dropwise, kept 15～20 ℃ of insulation reaction 4 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 600mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 144.7g(0.676mol), molar yield is 90.21%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 96.02%.HPLC external standard method testing conditions is with embodiment 1.
Embodiment 5
With acetone 600mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 200g(1.0mol), anhydrous sodium carbonate 159g(1.5mol), potassiumiodide 1.5g joins in the 2000mL four-hole reaction flask, 40～45 ℃ of slow methyl-sulfate 189g(1.5mol that drip of control temperature under the agitation condition), dropwise, kept 40～45 ℃ of insulation reaction 4 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 800mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 200.2g(0.9356mol), molar yield is 93.56%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 97.11%.HPLC external standard method testing conditions is with embodiment 1.
Embodiment 6
With acetone 825mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 300g(1.5mol), anhydrous sodium carbonate 254.4g(2.4mol), potassiumiodide 1.95g joins in the 2000mL four-hole reaction flask, 25～30 ℃ of slow methyl-sulfate 264.6g(2.1mol that drip of control temperature under the agitation condition), dropwise, kept 25～30 ℃ of insulation reaction 3 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 1200mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 298.5g(1.3947mol), molar yield is 92.98%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 96.51%.HPLC external standard method testing conditions is with embodiment 1.
Embodiment 7
With acetone 870mL, the 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone 300g(1.5mol), anhydrous sodium carbonate 270.3g(2.55mol), potassiumiodide 2.1g joins in the 2000mL four-hole reaction flask, 30～35 ℃ of slow methyl-sulfate 226.8g(1.8mol that drip of control temperature under the agitation condition), dropwise, kept 30～35 ℃ of insulation reaction 2 hours.Insulation reaction finishes, and negative pressure is concentrated steams acetone to the greatest extent, reclaims acetone, then add 1200mL water, rapid stirring, suction filtration separates, 60 ℃ of vacuum-dryings get the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone 299.4g(1.399mol), molar yield is 93.27%, detect through the HPLC external standard method, 4-amino-6-the tertiary butyl-3-methylthio group-1,2, the content of 4-triazine-5 (4H)-ketone is 97.05%.HPLC external standard method testing conditions is with embodiment 1.
The above only is preferred implementation of the present invention; should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the inventive method; can also make some improvement and replenish, these improvement and replenish and also should be considered as protection scope of the present invention.
Claims (10)
1. the 4-amino-6-tertiary butyl-3-methylthio group-1,2, the synthetic method of 4-triazine-5 (4H)-ketone, it is characterized in that, it is with acetone, 4-amino-6-the tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, anhydrous sodium carbonate and potassiumiodide join in the reactor, then control 15～45 ℃ of temperature under the agitation condition and drip methyl-sulfate, 15～45 ℃ of lower insulation reaction 2～5 hours, reclaim at last acetone after dropwising, add the elutriation material, separating also, drying obtains the 4-amino-6-tertiary butyl-3-methylthio group-1,2,4-triazine-5 (4H)-ketone, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, the mol ratio of methyl-sulfate and anhydrous sodium carbonate is 1:1.05～1.5:1.5～2.
2. synthetic method according to claim 1 is characterized in that, the consumption of described acetone is: the every mole of 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone is with 500～600 milliliters of acetone.
3. synthetic method according to claim 1 is characterized in that, the consumption of described potassiumiodide is: the every mole of 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone restrains potassiumiodide with 1～1.5.
4. synthetic method according to claim 1 is characterized in that, described temperature of reaction is 25～35 ℃.
5. synthetic method according to claim 1 is characterized in that, the described reaction times is 3～4 hours.
6. synthetic method according to claim 1 is characterized in that, described drying is 60 ℃ of vacuum-dryings.
7. synthetic method according to claim 1 is characterized in that, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, and the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.3:1.8.
8. synthetic method according to claim 1 is characterized in that, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, and the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.5:1.5.
9. synthetic method according to claim 1 is characterized in that, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, and the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.4:1.6.
10. synthetic method according to claim 1 is characterized in that, the described 4-amino-6-tertiary butyl-3-sulfydryl-1,2, and the mol ratio of 4-triazine-5 (4H)-ketone, methyl-sulfate and anhydrous sodium carbonate is 1:1.2:1.7.
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| 孙晓红 等: "选择性甲基化合成塞克津中间试验研究", 《化学工程》 * |
| 朱占元 等: "4-氨基-2-甲氧基-5-乙硫基苯甲酸的合成", 《淮阴工学院学报》 * |
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| CN103319424B (en) | 2016-01-20 |
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