CN106588785A - Preparation method of acetylpyrazine - Google Patents
Preparation method of acetylpyrazine Download PDFInfo
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- CN106588785A CN106588785A CN201611097102.5A CN201611097102A CN106588785A CN 106588785 A CN106588785 A CN 106588785A CN 201611097102 A CN201611097102 A CN 201611097102A CN 106588785 A CN106588785 A CN 106588785A
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- parts
- chloromethanes
- acetyl group
- toluene
- cyanopyrazine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of acetylpyrazine. Acetylpyrazine is prepared from 8-10 parts of magnesium chips, 180-200 parts of anhydrous tetrahydrofuran, 300-350 parts of chloromethane, 450-500 parts of anhydrous toluene, 20-25 parts of cyanopyrazine, 40-50 parts of alcohol, 2 parts of activated carbon and a plurality parts of chloromethane. Acetylpyrazine has the advantages that the synthesis method is simple, the raw materials are easy to obtain, energy consumption and material losses are low, the safety and the finished product content are high, and acetylpyrazine is suitable for large-scale production.
Description
Technical field：
Present invention relates particularly to a kind of preparation method of acetyl group pyrazine, belongs to chemical technology field.Acetyl group
Background technology：
Acetyl group pyrazine has quick-fried corn-like odor characteristic, 79～80 DEG C of fusing point, 57～58 DEG C of boiling point (0.8kPa), existing synthesis second
The preparation method of acyl group pyrazine has various, and one kind is to be dehydrated into corresponding nitrile by pyrazinamide, then with Grignard reagent methyl bromide
Change reactive magnesium, then hydrolyze and obtain.For edible essences such as Semen Maydiss, Semen Sesami, Semen arachidis hypogaeae, beef, it can also be used to flavouring essence for tobacco.In perfuming
Ultimate density normally only (1～5) mg/kg in food.In another kind of preparation method by chloromethanes and synthesizing methyl chlorination magnesium after, with
Cyanopyrazine is condensed, and then product is obtained after direct hydrolysis, extraction processing and terminates all to make solvent with ether.Because grignard reaction is to body
It is higher to be that moisture Control is required, each ether must strictly be dried and then just can reuse again after reclaiming, operate it is comparatively laborious,
Difficulty, energy consumption, loss of material are larger.Simultaneously ether boiling point is relatively low, and highly volatile, explosion limit is wider（1.9～36%）, endanger very much
Danger.
The content of the invention：
In view of this, the invention provides a kind of synthetic method is simple, raw material is easy to get, and energy consumption is little, and loss of material is less, safety
The preparation method of high acetyl group pyrazine.
For achieving the above object, the technical solution used in the present invention is：
A kind of preparation method of acetyl group pyrazine, is prepared from the following materials：8～10 parts of magnesium chips, anhydrous tetrahydro furan 180
～200 parts, it is 300～350 parts of chloromethanes, 450～500 parts of dry toluene, 20～25 parts of cyanopyrazine, 40～50 parts of ethanol, living
2 parts of charcoal of property, chloromethanes several pieces.
A kind of preparation method of acetyl group pyrazine, comprises the following steps：
1）50 parts with dry toluene of 20 parts of the cyanopyrazine for taking is sufficiently mixed, and makes mixed liquor standby；
2）1000ml there-necked flasks are taken, 9 parts of magnesium chips is added in bottle, be subsequently adding 180 parts of anhydrous tetrahydro furan, it is logical in 20～50 DEG C
Enter chloromethanes and make methyl-magnesium-chloride；
3）Add 400 parts of dry toluenes, 170～180 parts of heating Distillation recovery anhydrous tetrahydro furan；
4）Reclaim and finish 0～50 DEG C of temperature control, Deca step 1）Whole mixed liquors of gained, drop Bi Baowen 2～3 hours；
5）150 parts of Deca water is hydrolyzed, and with acetic acid PH=5～6 are neutralized to, then is extracted four times with 4 × 80 parts of toluene, removes first
Brownish red crude product is obtained after benzene；
6）By step 5) obtained by crude product and 50 parts of ethanol, 2 parts of activated carbons add there-necked flasks, stirring to be warming up to 60 DEG C, so
Filter off activated carbon with filter paper afterwards, it is mother liquid obtained to be cooled to 0～5 DEG C and separate out a large amount of white crystals, white crystalline body is filtered with filter paper
Go out, drying finished product acetyl group pyrazine.
The invention has the beneficial effects as follows：Synthetic method is simple, and raw material is easy to get, and energy consumption is little, and loss of material is less, safety
Height, finished product content is high, is adapted to large-scale production.
Specific embodiment:
To further elucidate this programme, the preferred embodiments of the invention are described with reference to specific embodiment, these descriptions
It is intended merely to further illustrate advantages of the present invention, rather than limiting to the claimed invention.
Embodiment 1
A kind of preparation method of acetyl group pyrazine, comprises the following steps：
1）The cyanopyrazine 20g for taking（0.19mol）It is sufficiently mixed with dry toluene 50g, makes mixed liquor standby；
2）1000g there-necked flasks are taken, magnesium chips 9g is added in bottle（0.37 mol）, anhydrous tetrahydro furan 180g is subsequently adding, in 20
～50 DEG C are passed through chloromethanes and make methyl-magnesium-chloride；
3）400g dry toluenes are added, Distillation recovery 170～180g of anhydrous tetrahydro furan is heated；
4）Reclaim and finish 0～50 DEG C of Deca step 1 of temperature control）Whole mixed liquors of gained, drop Bi Baowen 2～3 hours；
5）Deca water 150g is hydrolyzed, PH=5～6 is neutralized to acetic acid, then is extracted four times with 4 × 80g toluene, removes toluene
Brownish red crude product 15g, content 97% are obtained afterwards；
6）By step 5) obtained by 15g crude products and 50g ethanol, 2g activated carbons add there-necked flask, stirring be warming up to 60 DEG C, so
Filter off activated carbon with filter paper afterwards, it is mother liquid obtained to be cooled to 0～5 DEG C and separate out a large amount of white crystals, white crystalline body is filtered with filter paper
Go out, drying acetyl group pyrazine product about 12g, Han Liang≤99%.
Embodiment 2
A kind of preparation method of acetyl group pyrazine, comprises the following steps：
1）The cyanopyrazine 40kg for taking（0.38Kmol）It is sufficiently mixed with toluene 100L, makes mixed liquor standby；
2）Magnesium chips 18kg is added in reactor（0.74K mol）, anhydrous tetrahydro furan 360kg is subsequently adding, it is logical in 20 ~ 50 DEG C
Enter chloromethanes and make methyl-magnesium-chloride；
3）800kg dry toluenes are added, Distillation recovery 340 ~ 360kg of anhydrous tetrahydro furan is heated；
4）Reclaim and finish 0 ~ 50 DEG C of Deca step 1 of temperature control）Whole mixed liquors of gained, drop Bi Baowen 2 ~ 3 hours；
5）The kg of Deca water 300 is hydrolyzed, PH=5 ~ 6 are neutralized to 50 ~ 60kg of acetic acid, are extracted four times with 4 × 160m toluene, takes off
Except after toluene brownish red crude product 30kg, content 95 ~ 97%；
6）By step 5) obtained by 30kg crude products and 100kg ethanol, 4kg activated carbons add reactor stirring be warming up to 60 DEG C,
Then activated carbon is filtered off with filter paper, it is mother liquid obtained to be cooled to 0 ~ 5 DEG C and separate out a large amount of white crystals, white crystalline body is filtered with filter paper
Go out, drying 2- acetyl group pyrazine product about 24kg, Han Liang≤99%.
The use using low boiling point solvent ether is present invention obviates, tetrahydrofuran is used instead in the lattice for having strict anhydrous requirement
Recycle in the preparation reaction of formula reagent, without to solvent drying is repeated；Use toluene instead has water in hydrolysis and follow-up extraction etc.
Recycle in system, tetrahydrofuran（66 DEG C of boiling point）, toluene（110 DEG C of boiling point）Boiling point is higher, and volatility is less, greatly improves
The safety of operation.
The above is only the preferred embodiment of the present invention, above-mentioned preferred implementation is not construed as limitation of the present invention,
Protection scope of the present invention should be defined by claim limited range.For those skilled in the art come
Say, without departing from the spirit and scope of the present invention, the protection that some improvements and modifications also should be regarded as the present invention can also be made
Scope.
Claims (1)
1. a kind of preparation method of acetyl group pyrazine, it is characterised in that：It is prepared from the following materials：8～10 parts of magnesium chips, nothing
180～200 parts of water tetrahydrofuran, 300～350 parts of chloromethanes, 450～500 parts of dry toluene, 20～25 parts of cyanopyrazine, wine
Smart 40～50 parts, 2 parts of activated carbon, chloromethanes several pieces；The method is comprised the following steps：
1）50 parts with dry toluene of 20 parts of the cyanopyrazine for taking is sufficiently mixed, and makes mixed liquor standby；
2）1000ml there-necked flasks are taken, 9 parts of magnesium chips is added in bottle, be subsequently adding 180 parts of anhydrous tetrahydro furan, it is logical in 20～50 DEG C
Enter chloromethanes and make methyl-magnesium-chloride；
3）Add 400 parts of dry toluenes, 170～180 parts of heating Distillation recovery anhydrous tetrahydro furan；
4）Reclaim and finish 0～50 DEG C of temperature control, Deca step 1）Whole mixed liquors of gained, drop Bi Baowen 2～3 hours；
5）150 parts of Deca water is hydrolyzed, and with acetic acid PH=5～6 are neutralized to, then is extracted four times with 4 × 80 parts of toluene, removes first
Brownish red crude product is obtained after benzene；
6）By step 5) obtained by crude product and 50 parts of ethanol, 2 parts of activated carbons add there-necked flasks, stirring to be warming up to 60 DEG C, so
Filter off activated carbon with filter paper afterwards, it is mother liquid obtained to be cooled to 0～5 DEG C and separate out a large amount of white crystals, white crystalline body is filtered with filter paper
Go out, drying finished product acetyl group pyrazine.
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| CN201611097102.5A CN106588785A (en) | 2016-12-02 | 2016-12-02 | Preparation method of acetylpyrazine |
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| CN201611097102.5A CN106588785A (en) | 2016-12-02 | 2016-12-02 | Preparation method of acetylpyrazine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796416A (en) * | 2019-04-11 | 2019-05-24 | 河南蔚源生物科技有限公司 | A kind of synthetic method of 2- acetyl group pyrazine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016091776A1 (en) * | 2014-12-09 | 2016-06-16 | Evotec Ag | 1,3-thiazol-2-yl substituted benzamides |
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2016
- 2016-12-02 CN CN201611097102.5A patent/CN106588785A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016091776A1 (en) * | 2014-12-09 | 2016-06-16 | Evotec Ag | 1,3-thiazol-2-yl substituted benzamides |
Non-Patent Citations (3)
| Title |
|---|
| DEBNATH BHUNIYA，ET AL.: "Aminothiazoles: Hit to lead development to identify antileishmanial agents", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
| 徐玉明等: "3，5-二甲氧苯基己基酮的合成", 《广州化工》 * |
| 黄朋勉等: "3-甲基苯丙酮的合成方法研究", 《精细化工中间体》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796416A (en) * | 2019-04-11 | 2019-05-24 | 河南蔚源生物科技有限公司 | A kind of synthetic method of 2- acetyl group pyrazine |
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Application publication date: 20170426 |