Method for producing thiocarboxamidine salt compound

A technology for manufacturing methods and compounds, which is applied in the field of compounds of the formula, and can solve problems such as uneconomical, uneconomical, and unoptimized methods

Active Publication Date: 2020-08-14
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Long reaction time is not economical and not industrially preferred
In addition, the yield of Example 6 of Patent Document 2 is 59%. From the viewpoint of yield, the method of Patent Document 2 is also uneconomical and industrially unpreferable.

Method used

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  • Method for producing thiocarboxamidine salt compound
  • Method for producing thiocarboxamidine salt compound
  • Method for producing thiocarboxamidine salt compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0274] Production of [5,5-dimethyl(4,5-dihydroisoxazol-3-yl)]thioformamidine hydrochloride (5-a)

[0275] Step (C: Chlorination) and Step (D: Isothiouronium Formation)

[0276] [Chemical 51]

[0277]

[0278] (1) Production of 3-chloro-5,5-dimethyl-4,5-dihydroisoxazole (4-a)

[0279] Process (C: Chlorination)

[0280] 5,5-Dimethyl-4,5-dihydroisoxazole (3-a; 186mg, 1.88mmol, 100mol%) was dissolved in acetonitrile (0.94mL, 0.5L (liter) / mol, with (3- a) as the basis) and water (0.28mL, 0.15L / mol, based on (3-a)). Introduce chlorine gas therein at 25~30°C (as a gas of 50mL, metered with an airtight syringe at 25°C, gas specific gravity 2.935g / L (liter) (25°C), 0.147g, 2.07mmol, 110mol%), Stir at the same temperature for 1 hour. Production of the target 3-chloro-5,5-dimethyl-4,5-dihydroisoxazole (4-a) was confirmed by GC-MS analysis of the reaction mixture. As a result of GC analysis (area percentage) of the reaction mixture, the components other than the solvent etc. in the...

Embodiment 2～ Embodiment 21 and comparative example 1

[0287] Production of 3-chloro-5,5-dimethyl-4,5-dihydroisoxazole (4-a)

[0288] Process (C: Chlorination)

[0289] [Chemical 52]

[0290]

[0291] The chlorination of the process (C) was performed similarly to Example 1 (1) except having changed the solvent as shown in following Table 1. As a result of GC analysis (area percentage) of the reaction mixture, the target product, raw materials, and by-products other than these are shown in Table 1 below. In addition, the results of Example 1(1) are also shown in Table 1.

[0292] [Table 1]

[0293]

[0294] Uniformity ◯: The reaction liquid is uniform.

[0295] Uniformity ×: The reaction solution was separated into two layers.

[0296] The reaction proceeds when only a nitrile solvent is used as the reaction solvent. However by-products are also formed (cf. Example 2, Example 7, Example 16, Example 17 and Example 21). On the other hand, when only water was used as the reaction solvent, the yield was as low as 45% (see ...

Embodiment 22

[0298] Production of 3-chloro-5,5-dimethyl-4,5-dihydroisoxazole (4-a)

[0299] Process (C: Chlorination)

[0300] [Chemical 53]

[0301]

[0302] 5,5-Dimethyl-4,5-dihydroisoxazole (3-a; 5.0 g, 50.4 mmol, 100 mol%) was dissolved in acetonitrile (25 mL, 0.5 L (liter) / mol, with (3- a) as the basis) and water (10mL, 0.2L / mol, based on (3-a)). While stirring with a magnetic stirrer, introduce chlorine gas (2.6mL, liquefied and measured at -70°C, specific gravity 1.64 (-70°C), 4.3g, 60.5mmol, 120mol%) at 2-5°C for 30 minutes, Stir at the same temperature for 1 hour. As a result of GC analysis (area percentage) of the reaction mixture, the components other than the solvent etc. in the reaction mixture are as follows:

[0303] 3-Chloro-5,5-dimethyl-4,5-dihydroisoxazole (4-a: target product): 98%.

[0304] After the reaction, ethyl acetate (25mL), 1M sodium thiosulfate (Na 2 S 2 o 3 ) aqueous solution (5 mL) and saturated brine (10 mL) and stirred. The organic layer and the...

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Abstract

The present disclosure provides an industrially preferable, economical, and environmentally friendly method for producing a compound (C1) of formula (5), namely, a (4, 5-dihydroisooxazol -3-yl)thiocarboxamidine salt compound. The present disclosure relates to a method wherein: a reaction expressed by reaction formula (C2) is caused so as to produce a compound of formula (4) by reacting a compoundof formula (3) with a halogenation agent in the presence of a nitrile solvent, and the compound of formula (4) is subsequently reacted with a isothiouronium-forming agent, thereby producing a compoundof formula (5).

Description

technical field [0001] The present invention relates to a compound of formula (5), namely (4,5-dihydroisoxazol-3-yl)thioformamidine salt ((4,5-ヒヒドロイソオゾゾロ-3-イル) チオヒルボキサロ-3-イル) チオヒルボキサミロン A method for producing a compound, [0002] [chemical 1] [0003] [0004] In the formula, R 1 , R 2 and X as described later. Background technique [0005] The (4,5-dihydroisoxazol-3-yl)thioformamidine salt compound of formula (5) is useful as an intermediate for the production of pharmaceuticals, agricultural chemicals, and the like. WO2002 / 062770 (Patent Document 1) discloses useful herbicides. Among them, pyroxasulfone is widely known as a herbicide having excellent herbicidal activity. Furthermore, JP 2013-512201 (Patent Document 2) and WO2006 / 068092 (Patent Document 3) disclose that the compound of formula (5) is an important intermediate of the herbicide described in Patent Document 1. [0006] JP 2013-512201 (Patent Document 2) discloses a method for producing a (4,5-dihydroi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/04
CPCC07D261/04C07B61/00
Inventor 永田俊浩
Owner KUMIAI CHEM IND CO LTD
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