JPH02304065A - Production of 2-carbamoylimidazole-based compound - Google Patents

Abstract

PURPOSE:To obtain the subject compound useful as a raw material for agricultural chemicals, drugs, etc., industrially and advantageously by reacting a specific oxazole-based compound as a starting raw material with formamide or ammonium acetate. CONSTITUTION:An oxazole-based compound shown by formula I (R is alkyl; Z is alkyl phenyl which may be replaced with alkyl group or halogen atom) which as a starting raw material is reacted with formamide or ammonium acetate usually at 50 to 250 deg.C, preferably 100 to 210 deg.C to give a compound shown by formula II. The amount of formamide or ammonium acetate is 0.5 to 100mol based on 1mol compound shown by formula I. The compound shown by formula I is obtained by the reaction as shown by the reaction formula. In the reaction formula, an ethylphenacyloxamate may be cited as the compound shown by formula III.

Description

[Detailed description of the invention]

TECHNICAL FIELD The present invention relates to a method for producing 2-carbamoylimidazole compounds useful as raw materials for agricultural chemicals, medicines, and the like.

[Prior art]

As a method for producing an imidazole compound from an oxazole compound, for example,
Hemishe Berichte) Volume 86, 96-1
09 (1953) describes a method for obtaining an imidazole compound by reacting an oxazole compound and formamide under reflux. However, that document only discloses a method for converting an oxazole ring into an imidazole ring using a compound having a hydrogen atom or an alkyl group at the 2-position of the oxazole ring as a starting material; 2 of the imidazole ring using a compound having a -COOR group (R is an alkyl group)
No disclosure is made regarding a method for obtaining an imidazole compound having a carbamoyl crystal in the position. Furthermore, there is no disclosure of using ammonium acetate during the reaction. Furthermore, it is stated that in the reaction of an oxazole compound and bormamide, an imidazole compound may or may not be obtained depending on the change of the substituent on the oxazole ring. It seems difficult to predict.

[Tsuneki who led to this invention]

The present inventors conducted various tests to find an industrially advantageous production method for 2-carbamoylimidazole compounds, and found that the production method of the present invention described later can achieve the desired effects, and thus developed the present invention. completed.

[Disclosure of the invention]

The present invention provides an oxylyzole compound represented by the general formula (11) (wherein R is an alkyl or an alkyl group or a phenyl group substituted with a halogen atom and optionally carbonated) and boramamide or ammonium acetate. The present invention relates to a method for producing a 2-carbamoylimidazole compound represented by the formula (wherein Z is as described above), which comprises reacting the compound. In the general formula (1) and/or (II), the alkyl group represented by 1 and the alkyl group contained in Z are (J
Those with 1 to 6 carbon atoms, such as methyl, ethyl, and
Examples thereof include a cobyl group, a methyl group, a pentyl group, and a .\:1-yl group, which may be linear or have a side chain. In addition, examples of the halogen atom of soenyl h(, which may not be represented by Z and may be substituted with a halogen atom) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; In each case, they may be of the same type or different types. In the method of the present invention, hol J, amide, or ammonium acetate used in the reaction also functions as a solvent.
It is also possible to use °ζ without adding any other solvent, but it is also possible to appropriately select and use commonly used solvents as necessary. Use of hol 1, amide or ammonium nitrate used in the method of the present invention is from 0.5 to 100 per mole of the oni 1-sazole compound represented by the following general formula (TI). It is a mole. The reaction temperature in the method of the present invention (L) is usually 50 to 250°C.
, preferably 100 to 210°C, and the reaction time is usually 1 to 48 hours. The compound represented by the general formula (1) is described, for example, in Yakugaku Kanzume 76, pp. 305-306 (1956), Yakugaku Zasshi 9.
Volume 1, pp. 425-435 (1971), JP-A-Sho Go -
It can be produced by the following method, as described in Japanese Patent Application Laid-open No. 1173, Japanese Patent Application Laid-open No. 120873/1983, and the like. Z 0 2・. ri0\Cri
00 1 ll111 (II) (wherein Z and R are as described above)
Specifically, as the compound represented by I), for example, 2
Examples include -(1-oxycarbonyl)-5-phenyloxazole (melting point 6O-Gl'C), 2-(methoxycarbonyl)-5-phenyloxazole (melting point 95-96°C), and the general formula (III ), specifically, for example, ethyl phenacylox,
(melting point: 96-97°C), methyl phenacyloxamate (melting point: 10B-414°C), and the like. According to the method, general formula (IV)
It can be derived from the compound represented by (1”) (rV) (wherein,
(Z is as described in QiJ) Examples of the solvent used in the above reaction include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene;
Cyclic or acyclic aliphatic hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, n-hexano, cyclohexane, ethers such as diethyl ether, dioxane, tetrahydrofuran, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as acetonitrile, nitriles such as propionitrile, dimethylbormamide, N
-Aprotic polar solvents such as methylpyrrolidone, dimethyl sulfoxide, and sulfolane. Further, in the above reaction, an organic base such as pyridine may also be used. Furthermore, instead of POCl2, trichloroacetic anhydride, trichloroacetonitrile, trichloroacetyl chloride, oxalyl chloride, thionyl chloride, acetic anhydride, phosphorus trichloride, phosphorus pentoxide, phosphonitrilic chloride, phosgene (dimer), cyanuric chloride, tetrachloride Titanium, formic acid, etc. can also be used. Note that the compound represented by the above general formula (rV) can be derived into a compound useful as a fungicide for agricultural and horticultural use, etc., as described in European Patent Publication No. 298196. On the other hand, the compound represented by the general formula (1) produced by the method of the present invention can also be produced by a separate method such as coating. Otsu (V) (In the formula, Z is as described above) The compound represented by the above general formula (V) is described in Chemical Abstracts Vol. 58, 12527h (1963), Journal of Chemical Society (C) 1938-
1945 (1970), or by a method similar to that method, specifically, for example, 2-carbamoyl-5-phenyloxazole (melting point 189-191'C), 2 -Carbamoyl-5-methyloxazole (melting point: 163°C), 2-carbamoyl-5-(4-chlorophenyl)oxazole, and the like. Next, some examples of the method of the present invention will be described. Example 1 Production of 2-carbamoyl-4(5)-phenylimidazole 3.25 g of 2-(ethoxycarbonyl)-5-phenyloxazole and 30-formamide were mixed and heated at 150°C.
The mixture was allowed to react for 22 hours. After the reaction was completed, the cooled reaction product was poured into water and extracted with ethyl acetate. This organic layer was washed with water and dried over anhydrous sodium sulfate. The solid obtained by distilling off the solvent was washed with methylene chloride to obtain 1.6 g of the desired product. Example 2 Production of 2-carbamoyl-4(5)-phenylimidazole 3.25 g of 2-(ethoxycarbonyl)-5-phenyloxazole and 20 g of ammonium acetate were mixed with 12
After reacting at 0-130'C for 30 hours, the product was post-treated in the same manner as in Example 1 to obtain 1.9 g of the desired product. Patent applicant Ishihara Sangyo Co., Ltd. = 11-

Claims (1)

[Claims] 1. General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (II) (In the formula, R is an alkyl group, and Z is an alkyl group, an alkyl group, or a halogen atom. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A method for producing a 2-carbamoylimidazole compound represented by the formula (wherein Z is as described above).