CN105801437A - Synthetic method of (methylamino)(phenyl)methyl alcohol - Google Patents
Synthetic method of (methylamino)(phenyl)methyl alcohol Download PDFInfo
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- CN105801437A CN105801437A CN201610196852.1A CN201610196852A CN105801437A CN 105801437 A CN105801437 A CN 105801437A CN 201610196852 A CN201610196852 A CN 201610196852A CN 105801437 A CN105801437 A CN 105801437A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Abstract
The invention discloses a synthetic method of (methylamino)(phenyl)methyl alcohol, and belongs to the technical field of organic synthesis.The problems that in an existing (methylamino)(phenyl)methyl alcohol process, the yield is low, reaction time is long, a solvent cannot be recycled, and environmental pollution is likely to be caused are solved.
Description
Technical field
The invention discloses the synthetic method of one (methylamino) (phenyl) methanol, belong to technical field of organic synthesis.
Background technology
(methylamino) (phenyl) methanol is the antibacterial of a high activity, low toxicity, and has very strong preventive effect, and after dispenser, the lasting period is long, resistance of rainwater washing against, people and animals and other beneficial organism safeties are high, crop pollution is few, environmentally friendly etc..Cyazofamid is at home and abroad widely used in the downy mildew of the preventing and treating crop such as Fructus Cucumidis sativi, Fructus Vitis viniferae and the late blight of Fructus Lycopersici esculenti, potatoes and other crops.
(methylamino) (phenyl) methanol total recovery still can only achieve 38.9%, and the response time is longer, reaction additionally adopts N, N dimethylformamide makes solvent, reaction terminates rear reactant liquor and is directly discharged in water, and solvent cannot reclaim, and not only causes the waste of solvent, and make wastewater discharge strengthen, cause the huge pollution of environment.
Summary of the invention
The technical problem that present invention mainly solves: low for yield in (methylamino) (phenyl) Production of methanol at present, and the response time is long, solvent can not reclaim simultaneously, the problem easily causing environmental pollution, the invention provides the synthetic method of one (methylamino) (phenyl) methanol.
For reaching above-mentioned purpose, (methylamino) (phenyl) methanol-fueled CLC route of the present invention is:
In order to solve above-mentioned technical problem, the technical solution adopted in the present invention is:
(1) conical flask taking 50mL is dried in an oven; it is added thereto to 5～7mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 40～50mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 80～90 DEG C, heats 15～20min；
(2) after above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 2～4 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；
(3) (cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 1～3g is put in the beaker of 50mL, it is added thereto to 10～20mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 40～45 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 5～10mg graphite intercalation compound；
(4) after above-mentioned interpolation completes; beaker is loaded onto gas concentration unit; beaker is warming up to 50～55 DEG C; use nitrogen protection simultaneously, after keeping temperature 40～50min, load onto reflux; it is warming up to 90～95 DEG C; keep temperature 50～60min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；
(5) backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 10～15mL, and the manganese dioxide of 10～15mg, stir, be then added thereto to the potassium chlorate of 1～4mg and 1～3 zeolite again, reflux is loaded onto subsequently at there-necked flask, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collect backflow, (methylamino) (phenyl) methanol yield can be obtained and reach 59～67%.
The invention has the beneficial effects as follows:
(1) present invention makes simply, it is easy to operation；
(2) product obtained by the present invention, yield reaches 59～67%.
Detailed description of the invention
The conical flask taking 50mL is dried in an oven; it is added thereto to 5～7mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 40～50mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 80～90 DEG C, heats 15～20min；After above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 2～4 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；(cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 1～3g is put in the beaker of 50mL, it is added thereto to 10～20mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 40～45 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 5～10mg graphite intercalation compound；After above-mentioned interpolation completes; beaker is loaded onto gas concentration unit; beaker is warming up to 50～55 DEG C; use nitrogen protection simultaneously, after keeping temperature 40～50min, load onto reflux; it is warming up to 90～95 DEG C; keep temperature 50～60min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；The backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 10～15mL and the manganese dioxide of 10～15mg, stirs, then the potassium chlorate of 1～4mg and 1～3 zeolite it are added thereto to again, loading onto reflux at there-necked flask subsequently, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collecting backflow, can obtain (methylamino) (phenyl) methanol, yield reaches 59～67%.
Example 1
The conical flask taking 50mL is dried in an oven; it is added thereto to 5mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 50mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 80 DEG C, heats 15min；After above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 4 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；(cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 1g is put in the beaker of 50mL, it is added thereto to 10mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 45 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 10mg graphite intercalation compound；After above-mentioned interpolation completes, beaker is loaded onto gas concentration unit, beaker is warming up to 50 DEG C, use nitrogen protection simultaneously; after keeping temperature 40min, load onto reflux, be warming up to 95 DEG C; keep temperature 50min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；The backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 10mL and the manganese dioxide of 15mg, stirs, then the potassium chlorate of 4mg and 1 zeolite it are added thereto to again, loading onto reflux at there-necked flask subsequently, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collecting backflow, can obtain (methylamino) (phenyl) methanol, yield reaches 64.2%.
Example 2
The conical flask taking 50mL is dried in an oven; it is added thereto to 7mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 50mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 90 DEG C, heats 20min；After above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 4 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；(cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 3g is put in the beaker of 50mL, it is added thereto to 20mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 45 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 10mg graphite intercalation compound；After above-mentioned interpolation completes, beaker is loaded onto gas concentration unit, beaker is warming up to 55 DEG C, use nitrogen protection simultaneously; after keeping temperature 50min, load onto reflux, be warming up to 95 DEG C; keep temperature 60min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；The backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 15mL and the manganese dioxide of 15mg, stirs, then the potassium chlorate of 4mg and 1～3 zeolite it are added thereto to again, loading onto reflux at there-necked flask subsequently, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collecting backflow, can obtain (methylamino) (phenyl) methanol, yield reaches 67%.
Example 3
The conical flask taking 50mL is dried in an oven; it is added thereto to 5mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 40mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 80 DEG C, heats 15min；After above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 2 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；(cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 1g is put in the beaker of 50mL, it is added thereto to 10mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 40 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 5mg graphite intercalation compound；After above-mentioned interpolation completes, beaker is loaded onto gas concentration unit, beaker is warming up to 50 DEG C, use nitrogen protection simultaneously; after keeping temperature 40min, load onto reflux, be warming up to 90 DEG C; keep temperature 50min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；The backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 10mL and the manganese dioxide of 10mg, stirs, then the potassium chlorate of 1mg and 1 zeolite it are added thereto to again, loading onto reflux at there-necked flask subsequently, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collecting backflow, can obtain (methylamino) (phenyl) methanol, yield reaches 59%.
Claims (1)
1. the synthetic method of (methylamino) (phenyl) methanol, it is characterised in that concrete synthesis step is:
(1) conical flask taking 50mL is dried in an oven; it is added thereto to 5～7mL (Z)-N-methyl isophthalic acid-phenyl azomethine and 40～50mg sodium cyanoborohydride respectively; conical flask is jiggled with hands; make the sodium cyanoborohydride in conical flask be completely dissolved, subsequently conical flask is moved in water-bath, be heated; nitrogen is used to be discharged by the air in conical flask; carrying out nitrogen protection, design temperature is 80～90 DEG C, heats 15～20min；
(2) after above-mentioned heating terminates, it is added thereto to frozen water, use Glass rod is stirred, until producing without precipitation, then decompression sucking filtration is carried out, material after use frozen water flushing sucking filtration 2～4 times, dries sucking filtration residue subsequently, can obtain (cyano group (phenyl) methyl) (methyl) amide；
(3) (cyano group (phenyl) methyl) (methyl) amide weighing the above-mentioned gained of 1～3g is put in the beaker of 50mL, it is added thereto to 10～20mL dichloromethane again, subsequently beaker is moved in water-bath and be heated, temperature is set as 40～45 DEG C, use Glass rod to be slowly stirred until the solid in beaker is completely dissolved, be then added thereto to 5～10mg graphite intercalation compound；
(4) after above-mentioned interpolation completes; beaker is loaded onto gas concentration unit; beaker is warming up to 50～55 DEG C; use nitrogen protection simultaneously, after keeping temperature 40～50min, load onto reflux; it is warming up to 90～95 DEG C; keep temperature 50～60min, collect backflow, 2-methylamino-2-phenylacetonitrile can be obtained；
(5) backflow of above-mentioned gained is put in three mouthfuls of beakers, it is added thereto to the deionized water of 10～15mL and the manganese dioxide of 10～15mg, stirs, then the potassium chlorate of 1～4mg and 1～3 zeolite it are added thereto to again, loading onto reflux at there-necked flask subsequently, being warming up to reflux has backflow to produce, and keeps temperature, until producing without backflow, collecting backflow, can obtain (methylamino) (phenyl) methanol, yield reaches 59～67%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610196852.1A CN105801437A (en) | 2016-03-31 | 2016-03-31 | Synthetic method of (methylamino)(phenyl)methyl alcohol |
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| CN201610196852.1A CN105801437A (en) | 2016-03-31 | 2016-03-31 | Synthetic method of (methylamino)(phenyl)methyl alcohol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113784944A (en) * | 2019-04-17 | 2021-12-10 | 纽朗制药公司 | Process for producing substituted 2- [2- (phenyl) ethylamino ] alkanamide derivatives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1850781A (en) * | 2006-05-22 | 2006-10-25 | 浙江苏泊尔制药有限公司 | Method for preparing venlafaxin |
| JP2011068693A (en) * | 2011-01-07 | 2011-04-07 | Kanto Denka Kogyo Co Ltd | New biphenyl compound having reaction-active group |
| CN103351311A (en) * | 2013-06-17 | 2013-10-16 | 张家港威胜生物医药有限公司 | Synthesis method of diphenylacetonitrile |
-
2016
- 2016-03-31 CN CN201610196852.1A patent/CN105801437A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1850781A (en) * | 2006-05-22 | 2006-10-25 | 浙江苏泊尔制药有限公司 | Method for preparing venlafaxin |
| JP2011068693A (en) * | 2011-01-07 | 2011-04-07 | Kanto Denka Kogyo Co Ltd | New biphenyl compound having reaction-active group |
| CN103351311A (en) * | 2013-06-17 | 2013-10-16 | 张家港威胜生物医药有限公司 | Synthesis method of diphenylacetonitrile |
Non-Patent Citations (6)
| Title |
|---|
| KOEPPEN, JUERGEN等: "N-acyl-α-imino acid derivatives. II. Synthesis of N-acylimines of methyl phenylglyoxylate", 《LIEBIGS ANNALEN DER CHEMIE》 * |
| P.L.ZHU等: "Combined use of temperature and solvent strength in reversed-phase gradient elution I.Predicting separation as a function of temperature and gradient conditions", 《JOURNAL OF CHROMATOGRAPHY A.》 * |
| PRESCIMONE, ALESSANDRO等: "High-pressure study of oxo-bridged mixedvalent MnIII/MnIV dimmers", 《ZEITSCHRIFT FUER NATURFORSCHUNG, B: A JOURNAL OF CHEMICAL SCIENCES》 * |
| VIDAL, JOELLE等: "N-Alkyloxycarbonyl-3-aryloxaziridines: their preparation, structure, and utilization as electrophilic amination reagents", 《CHEM. EUR. J.》 * |
| WOOD,C.E.，LILLEY,H.S.: "Transformation of Mandelonitrile into Mandeloisonitrile", 《JOURNAL OF THE CHEMICAL SOCIETY, TRANSACTIONS》 * |
| 胡跃飞: "《现代有机合成试剂 2 还原反应试剂》", 31 July 2011, 化学工业出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113784944A (en) * | 2019-04-17 | 2021-12-10 | 纽朗制药公司 | Process for producing substituted 2- [2- (phenyl) ethylamino ] alkanamide derivatives |
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