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Process for producing benzylamine derivative

一种衍生物、苄胺的技术，应用在制备苄胺衍生物领域，能够解决工序数目长、位置选择性低、不能稳定地保持氨基甲酸酯基等问题

Inactive Publication Date: 2006-07-12
IHARA CHEM IND CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in the method of [Chemical Formula 8] of the former Patent Document 1, in the preparation of the raw material of the toluene derivative having an acyl group, since the position selectivity is low when the acyl nucleus is introduced, positional isomers are produced by-products, which inevitably make the Acyl derivatives of toluene target product yield decreased
In addition, in the method of [Chemical Formula 9] of the latter Patent Document 1, the number of steps is relatively long, and since the carbamate group itself is subjected to severe conditions in acid and alkali, the following problems arise: it cannot be stably Retention of carbamate groups occurs in cases where carbamate groups are decomposed under reaction conditions
In addition, using any method, the yield of all processes from raw materials is not high enough, and improvement is also needed in this respect

Method used

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  • Process for producing benzylamine derivative
  • Process for producing benzylamine derivative
  • Process for producing benzylamine derivative

Examples

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preparation example Construction

[0106] The preparation of the benzylamine derivative represented by the general formula (3) is as described in the above [1].

[0107] (hydrolysis)

[0108] The preparation of the amino derivative represented by the general formula (4) by hydrolyzing the benzylamine derivative represented by the general formula (3) obtained in the above-mentioned present invention [1] will now be described.

[0109] The method for hydrolyzing the benzylamine derivative represented by the general formula (4) is not particularly limited, but it is preferably carried out using Bronsted acid from the viewpoint of easy availability.

[0110] (Bronsted acid)

[0111] Examples of the Bronsted acid that can be used in the hydrolysis reaction include aliphatic carboxylic acids that may be substituted with halogen such as acetic acid, propionic acid, and trifluoroacetic acid; and inorganic acids such as sulfuric acid and hydrochloric acid. Among them, inorganic acids are preferred, and sulfuric acid i...

Embodiment 1

[0170] 1) Preparation of N-[(5-acetyl-2-chlorophenyl)methyl]acetamide (compound 3):

[0171] (Invention described in item [1])

[0172] 36.7g (0.2 moles) of N-[(2-chlorophenyl)methyl]acetamide was dissolved in 60ml of dichloromethane, and 80.0g (0.6 moles) of aluminum chloride was added over 30 minutes at 5-30°C, 31.4 g (0.4 mol) of acetyl chloride was added dropwise at the same temperature over 30 minutes.

[0173] After aging at room temperature for 1 hour, the temperature was raised to the heating reflux temperature in 15 minutes, and aging was carried out for 12 hours under the heating reflux condition. After the reaction, the resulting reaction solution was poured into water, extracted three times with 50 ml of toluene, and the solvent was distilled off under reduced pressure. The residue was cooled, and the precipitated crystals were filtered out, washed with toluene, and dried to obtain 24.5 g (yield: 54.3%, purity: 99.4%) of the target compound (melting point: 93.1-9...

Embodiment 2

[0176] Preparation of N-[(5-acetyl-2-chlorophenyl)methyl]methoxycarboxamide

[0177] (A)) Preparation of 1-[3-(aminomethyl)-4-chlorophenyl]]ethan-1-one (compound 1) (invention according to item [6])

[0178] After 20.0g (0.089 moles) of N-[(5-acetyl-2-chlorophenyl) methyl] acetamide prepared by embodiment 1 was dissolved in 50% sulfuric acid of 55g, heated to reflux through 30 minutes Temperature, aging under reflux conditions for 15 hours.

[0179] After the reaction, the resulting reaction solution was poured into water, 45 ml of toluene was added, and the aqueous solution was adjusted to be alkaline (pH=12.0) with 25% sodium hydroxide. After extraction twice with 45 ml of toluene, the solvent was distilled off under reduced pressure to obtain the title compound almost quantitatively (purity: 99.2%).

[0180] MS(GC-MS)m / z=182(M + -1), 140 (base peak).

[0181] (B) Production method of N-[(5-acetyl-2-chlorophenyl)methyl]methoxycarboxamide (invention described in item [7])...

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Abstract

Disclosed is a process for producing a benzylamine derivative represented by the general formula (3): which is characterized by comprising reacting a benzyl derivative represented by the general formula (1) with the acyl halide compound represented by the general formula (2) when Lewis acid exists: wherein X<1> represents a halogen atom and R<1> represents an acyl group, with a haloacyl compound represented by the general formula (2):R2-X2, wherein X<2> represents a halogen atom and R<2> represents an acyl group. According to this method, a benzylamine derivative as an intermediate, which is useful for the preparation of a carbamate-based agricultural or horticultural bactericide, can be preferably prepared.

Description

technical field [0001] The present invention relates to a method for preparing benzylamine derivatives, a method for preparing carbamate derivatives by the same, and intermediates useful in the method for preparing carbamate derivatives. The benzylamine derivatives prepared by the present invention are, for example, useful intermediates for the preparation of carbamate fungicides for agriculture and horticulture. Background technique [0002] Conventionally, as a method for preparing carbamate-type agricultural and horticultural fungicides, known: ① by making the carbamate derivative represented by the following general formula (6) of the present application react with hydroxylamine or its derivative (Refer to the preparation method 1 of Patent Document 1); and ② make α-halogenated toluene derivatives by halogenation of toluene derivatives, after further reacting with potassium cyanate etc. for carbamateization, introduce nitro groups to make A production method in which th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/62C07C211/29C07C231/12C07C233/31C07C269/04C07C271/18
CPCC07C233/31C07C231/12C07C209/62C07C211/29C07C271/18C07C269/04
Inventor 伊藤彰记大桥秀昭曲渕景友
Owner IHARA CHEM IND CO LTD
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