CN102391187A - Preparation method of N-(2-propinyl)-glycolylurea - Google Patents
Preparation method of N-(2-propinyl)-glycolylurea Download PDFInfo
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- CN102391187A CN102391187A CN2011102511493A CN201110251149A CN102391187A CN 102391187 A CN102391187 A CN 102391187A CN 2011102511493 A CN2011102511493 A CN 2011102511493A CN 201110251149 A CN201110251149 A CN 201110251149A CN 102391187 A CN102391187 A CN 102391187A
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Abstract
The invention discloses a preparation method of N-(2-propinyl)-glycolylurea. The preparation method comprises the following steps of: (1) dissolving N-(2-propinyl)-N-carbethoxyl amino-acetonitrile into a solvent, adding an aid, heating to 20-80 DEG C, dropwise adding an alkaline catalyst, preserving heat and undergoing a ring-closure reaction; and (2) cooling the obtained reaction liquid to the room temperature, dropwise adding acid for neutralizing till the pH is 6-8, distilling under reduced pressure to remove ethanol serving as a byproduct, cooling to 0-10 DEG C, separating crystals out, preserving heat at 0-10 DEG C till no crystal can be separated out, and drying the crystals to obtain N-(2-propinyl)-glycolylurea. The N-(2-propinyl)-glycolylurea prepared with the method has the characteristics of simple process, safety for operating, high yield, low cost and low emission of three wastes.
Description
Technical field
The present invention relates to a kind of compound method of organic cpds, particularly N-(2-propynyl)-NSC 9226 (having another name called the alkynes glycolylurea) (1-(prop-2-ynyl) imidazolidine-2, compound method 4-dione).
Background technology
N-(2-propynyl)-NSC 9226, its molecular formula is C
6H
6O
2N
2, its structural formula is shown in S-1, and pure article are that white is to the pearl crystallization; Fusing point 124-125 ℃, be slightly soluble in ethanol, ETHYLE ACETATE, be dissolved in cold water hardly; It is a kind of important fine-chemical intermediate; Application aspect medicine, agricultural chemicals and chemosynthesis is particularly popular, is mainly used in the efficient glycolylurea insecticides of synthesizing new, disinfectant, and as products such as the optical activity catalyzer in the chemosynthesis, peptizing agents.
The comprehensive literature report, the comparatively typical preparation method of NSC 9226 has at present:
(1), EP0560622, JP5255272, disclosing a kind of is raw material with the glycolylurea; Obtain morpholinyl Methylimidazole alkane-2 with morpholine, 37% formaldehyde solution low-temp reaction in polar solvent; The 4-diketone, products therefrom reacts with methylsulfonic acid alkynes propyl ester in polar solvent under katalysis then; Obtain title product, reaction formula is shown in S-2;
(2), US5883260 discloses another kind of compound method, this method is a raw material with the aminoacetonitriles hydrochloride, with the Vinyl chloroformate condensation, acidifying promptly obtains title product under catalyst action, reaction formula is shown in S-3
(3), to disclose a kind of be raw material with N-proyl glycine ethyl ester to CN1446805; Reaction generates N-propargyl-N-formamido group ETHYLE ACETATE with potassium cyanate; Under the condition that catalyst acid (for example Hydrogen bromide) exists, carry out cyclization again and generate title product, reaction formula is shown in S-4.
The first method raw material is not easy to obtain, and toxicity is big, and cost is high, and is less economical; Vinyl chloroformate, 3-chloroallylene are poisonous inflammable liquid in the second method, and easy explosion caused accident manipulates being absolutely unsafe, reaction yield low (being merely 63%); Though the third method yield can reach 90.1%, used the reaction of toxic substance potassium cyanate in the reaction process, environmental pollution is bigger; And because Hydrogen bromide has severe corrosive, be prone to decompose, to equipment requirements than higher.
Summary of the invention
The technical problem that the present invention will solve provides that a kind of technology is succinct, the preparation method of operational safety, yield is high, cost is low, three waste discharge is few N-(2-propynyl)-NSC 9226.
In order to solve the problems of the technologies described above, the present invention provides the preparation method of a kind of N-(2-propynyl)-NSC 9226, may further comprise the steps:
1), N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is dissolved in solvent, adds auxiliary agent, drips basic catalyst after being heated to 20～80 ℃, ring-closure reaction is carried out in insulation; The time of ring-closure reaction is 1～6h; The mol ratio of auxiliary agent and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 1～10: 1, and the ratio of the mole of basic catalyst and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 1～1.5: 1;
2), the gained reaction solution is cooled to room temperature; Drip acid again and be neutralized to pH=6～8; Then underpressure distillation removes the ethanol as by product, is cooled to 0～10 ℃ and begins to separate out crystal, and 0～10 ℃ of insulation is until no longer separating out crystal (general about 0.5～1.0h); Crystal is dry, obtain N-(2-propynyl)-NSC 9226.
Improvement as the preparation method of N-of the present invention (2-propynyl)-NSC 9226: auxiliary agent is hydrogen peroxide, liquefied ammonia, urea, yellow soda ash or bicarbonate of ammonia; Basic catalyst is sodium hydroxide, Pottasium Hydroxide, sodium methylate, sodium ethylate or sodium-acetate.
Further improvement as the preparation method of N-of the present invention (2-propynyl)-NSC 9226: the ratio of the quality of solvent and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 2～5: 1.
Further improvement as the preparation method of N-of the present invention (2-propynyl)-NSC 9226: solvent is a water.
Further improvement as the preparation method of N-of the present invention (2-propynyl)-NSC 9226: be used for neutral acid and be 10%～50% inorganic acid solution for mass concentration.
Further improvement as the preparation method of N-of the present invention (2-propynyl)-NSC 9226: mineral acid is hydrochloric acid, sulfuric acid or Hydrogen bromide.
In step 1) of the present invention, the optimum temps of ring-closure reaction is 45～70 ℃, and the reaction times is 1.5～5.5h.
In sum, the present invention is a raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, is dissolved in solvent and adds auxiliary agent, is heated to specified temp, slowly splashes into the adding basic catalyst, stopped reaction behind the certain hour; The reaction solution underpressure distillation is removed ethanol, drip sour neutralization reaction liquid again to pH=6-8, be cooled to 0-10 ℃, slowly separate out crystal, filter, drying obtains product.
The reaction equation that the present invention prepares N-(2-propynyl)-NSC 9226 is following:
It is raw material that the present invention adopts with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, under solvent and auxiliary agent condition, obtains acid amides through base catalysis; With after the acid neutralization, Cheng Huan obtains product then.This method is used nontoxicity reagent, is the approach of an environmental friendliness, operational safety.
The preparation method of N-of the present invention (2-propynyl)-NSC 9226 has following advantage:
1, adopt water as solvent, add auxiliary agent, be reflected under the normal pressure and carry out, facility investment is little, and technology is simple, and is safe;
2, be catalyzer with common alkaline matter, do not need pre-treatment step such as Preparation of Catalyst, cost is low, and is easy and simple to handle;
3, the product aftertreatment is simple, and reaction yield is high, good product quality, and the alcohols of products production can be recycled, and does not have other by products, does not produce the waste gas waste residue, green non-pollution.
Embodiment
The preparation method of embodiment 1, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 33mL water and make solvent, feed auxiliary agent liquefied ammonia 1mol, mixed solution is divided into two phases; Be heated to 45～50 ℃, slowly drip massfraction and be 30% sodium hydroxide solution 16.7g, about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 5.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=7); Decompression (ethanol (50～55 ℃ of still temperature) as by product is reclaimed in 10～20KPa) distillations, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Treat that (time was about 0.5～1.0h) suction filtration when solution was no longer separated out crystal; Yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 12.5g, productive rate 90.6%; Fusing point is 123.3-124.5 ℃, and purity is 99%.
The preparation method of embodiment 2, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, 40mL water is made solvent, and adding the auxiliary agent massfraction is 30% hydrogen peroxide 22.6g; Mixed solution is divided into two phases, is heated to 45～50 ℃, slowly drips massfraction and be 30% sodium hydroxide solution 16.7g; About 10min dropwises, and reaction solution becomes homogeneous phase mutually by two, and color is by the orange-yellow brown that becomes; Gradually become Vandyke brown; GC detection reaction process continues reaction 4.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=6); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 10.5g; Productive rate 74.6%, fusing point are 122.6-124.0 ℃, and purity is 98%.
The preparation method of embodiment 3, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 50mL water and make solvent, splashing into the auxiliary agent massfraction is 30% hydrogen peroxide 11.3g; Mixed solution is divided into two phases, is heated to 45～50 ℃, slowly drips massfraction and be 30% sodium hydroxide solution 16.7g; About 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color is by the orange-yellow deep yellow look that gradually becomes, GC detection reaction process; Continue reaction 4.5h, temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=8); Decompression (ethanol (50～55 ℃ of still temperature) as by product is reclaimed in 10～20KPa) distillations, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 11.1g; Productive rate 80.4%, fusing point are 123.0-124.5 ℃, and purity is 99%.
The preparation method of embodiment 4, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 60mL water and make solvent, add auxiliary agent urea 0.2mol, mixed solution is divided into two phases; Be heated to 45～50 ℃, slowly drip massfraction and be 30% sodium hydroxide solution 20.0g, about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 4.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 30% hydrobromic acid solution neutralization reaction liquid (to pH=7.5); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 10.8g; Productive rate 78.3%, fusing point are 123.2-124.5 ℃, and purity is 99%.
The preparation method of embodiment 5, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 35mL water and make solvent, add auxiliary agent yellow soda ash 0.1mol, mixed solution is divided into two phases; Be heated to 55～60 ℃, slowly drip mass concentration and be 30% sodium hydroxide solution 16.7g, about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 3.5h, and temperature of reaction is 55～60 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using mass concentration again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=6.5); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 10.4g; Productive rate 75.4%, fusing point are 123.7-124.7 ℃, and purity is 98%.
The preparation method of embodiment 6, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 83mL water and make solvent, add auxiliary agent bicarbonate of ammonia 0.4mol; Mixed solution is divided into two phases, is heated to 35～40 ℃, slowly drips massfraction and be 30% sodium hydroxide solution 13.3g; About 10min dropwises, and reaction solution becomes homogeneous phase mutually by two, and color is by the orange-yellow brown that becomes; Gradually become Vandyke brown; GC detection reaction process continues reaction 5.5h, and temperature of reaction is 35～40 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=7); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 9.7g; Productive rate 70.3%, fusing point are 124.1-125.3 ℃, and purity is 99%.
The preparation method of embodiment 7, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 70mL water and make solvent, feed auxiliary agent liquefied ammonia 1mol, mixed solution is divided into two phases; Be heated to 65～70 ℃, slowly dripping massfraction is 30% potassium hydroxide solution 18.7g, and about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 1.5h, and temperature of reaction is 65～70 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 20% sulfuric acid neutralization reaction liquid (to pH=7); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 12.3g; Productive rate 89.1%, fusing point are 123.8-125.1 ℃, and purity is 97%.
The preparation method of embodiment 8, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 60mL water and make solvent, feed auxiliary agent liquefied ammonia 0.8mol, mixed solution is divided into two phases; Be heated to 45～50 ℃, slowly dripping massfraction is 30% sodium methoxide solution 27g, and about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 4.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=7); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 10.0g; Productive rate 72.5%, fusing point are 123.7-125.1 ℃, and purity is 97%.
The preparation method of embodiment 9, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 50mL water and make solvent, feed auxiliary agent liquefied ammonia 0.7mol, mixed solution is divided into two phases; Be heated to 45～50 ℃, slowly drip 30% alcohol sodium solution 28.3g, about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 3.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 225 ℃ of room temperatures, and using mass concentration again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=7); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to room temperature 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 10.4g; Productive rate 75.4%, fusing point are 123.7-124.9 ℃, and purity is 98%.
The preparation method of embodiment 10, a kind of N-(2-propynyl)-NSC 9226 is a starting raw material with N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile, carries out following steps successively:
(1) 16.6g (0.1mol) N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is joined in the 250mL flask, add 50mL water and make solvent, feed auxiliary agent liquefied ammonia 1mol, mixed solution is divided into two phases; Be heated to 45～50 ℃, slowly dripping massfraction is 30% sodium acetate soln 34.2g, and about 10min dropwises; Reaction solution becomes homogeneous phase mutually by two, and color gradually becomes Vandyke brown by the orange-yellow brown that becomes; GC detection reaction process continues reaction 1.5h, and temperature of reaction is 45～50 ℃;
(2) reaction finishes, and is cooled to 25 ℃ of room temperatures, and using massfraction again is 35% hydrochloric acid soln neutralization reaction liquid (to pH=7); The ethanol (50～55 ℃ of still temperature) as by product is reclaimed in underpressure distillation, still liquid be cooled to 0-10 ℃ slowly stirring separate out crystal, in 0-10 ℃ of insulation; Suction filtration when treating that solution is no longer separated out crystal, yellow crystals, weigh after the drying product N-(2-propynyl)-NSC 9226 9.5g; Productive rate 69%, fusing point are 123.6-125.3 ℃, and purity is 97%.
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (6)
1.N-the preparation method of (2-propynyl)-NSC 9226 is characterized in that may further comprise the steps:
1), N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is dissolved in solvent, adds auxiliary agent, drips basic catalyst after being heated to 20～80 ℃, ring-closure reaction is carried out in insulation; The time of ring-closure reaction is 1～6h; The mol ratio of said auxiliary agent and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 1～10: 1, and the ratio of the mole of said basic catalyst and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 1～1.5: 1;
2), the gained reaction solution is cooled to room temperature, drips acid again and be neutralized to pH=6～8, then underpressure distillation removes the ethanol as by product; Be cooled to 0～10 ℃ and begin to separate out crystal; 0～10 ℃ of insulation is until no longer separating out crystal, and crystal is dry, obtains N-(2-propynyl)-NSC 9226.
2. the preparation method of N-according to claim 1 (2-propynyl)-NSC 9226 is characterized in that: said auxiliary agent is hydrogen peroxide, liquefied ammonia, urea, yellow soda ash or bicarbonate of ammonia; Said basic catalyst is sodium hydroxide, Pottasium Hydroxide, sodium methylate, sodium ethylate or sodium-acetate.
3. the preparation method of N-according to claim 2 (2-propynyl)-NSC 9226 is characterized in that: the ratio of the quality of said solvent and N-(2-propynyl)-N-ethoxycarbonyl amino-acetonitrile is 2～5: 1.
4. according to the preparation method of claim 2 or 3 described N-(2-propynyl)-NSC 9226, it is characterized in that: said solvent is a water.
5. the preparation method of N-according to claim 4 (2-propynyl)-NSC 9226 is characterized in that: said to be used for neutral acid be 10%～50% inorganic acid solution for mass concentration.
6. the preparation method of N-according to claim 5 (2-propynyl)-NSC 9226 is characterized in that: said mineral acid is hydrochloric acid, sulfuric acid or Hydrogen bromide.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172804A (en) * | 1996-06-24 | 1998-02-11 | 住友化学工业株式会社 | Process for producing 1 -substituted -hydantoins |
| CN1446805A (en) * | 2003-04-09 | 2003-10-08 | 中山市凯达精细化工股份有限公司 | Method for preparing 1-proparagyl hydantoin |
-
2011
- 2011-08-29 CN CN2011102511493A patent/CN102391187A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172804A (en) * | 1996-06-24 | 1998-02-11 | 住友化学工业株式会社 | Process for producing 1 -substituted -hydantoins |
| CN1446805A (en) * | 2003-04-09 | 2003-10-08 | 中山市凯达精细化工股份有限公司 | Method for preparing 1-proparagyl hydantoin |
Non-Patent Citations (2)
| Title |
|---|
| 《J.Am.Chem.Soc.》 19170131 L. McMASTER, et al. "THE TRANSFORMATION OF NITRILES INTO AMIDES BY HYDROGEN PEROXIDE" p103-109 1-6 第39卷, 第1期 * |
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Application publication date: 20120328 |