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A process for preparing anthranilic diamides and intermediates thereof

A technology of o-formamidobenzamide and compounds, which is applied in the field of preparation of o-formamidobenzamide compounds, and can solve problems such as laborious methods and lack of selectivity

Pending Publication Date: 2021-11-23
PI IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the methods described in the above documents are laborious or lack sufficient selectivity, and there is still a need to find a simple, efficient and industrially economical method for the preparation of o-carboxamidobenzamides

Method used

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  • A process for preparing anthranilic diamides and intermediates thereof
  • A process for preparing anthranilic diamides and intermediates thereof
  • A process for preparing anthranilic diamides and intermediates thereof

Examples

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Embodiment 1

[0100] Step A: Preparation of 2-(hydroxyimino)-N-(o-tolyl)acetamide

[0101] To a solution of o-toluidine (75 g, 700 mmol) in water (170 mL) was slowly added hydrochloric acid (73 g, 700 mmol, 35% w / w), followed by anhydrous sodium sulfate (636 g, 4478 mmol) in water (800 mL). The resulting reaction mixture was heated to 55 °C. An aqueous solution of hydroxylamine hydrochloride (73 g, 1050 mmol) in water (280 mL) was then added slowly, followed by a solution of chloral hydrate (125 g, 757 mmol) in water (270 mL). The reaction mixture was maintained at 55°C for 12 hours. After the reaction was complete, the reaction mixture was cooled to 20 °C and stirred for 1 hour. The solid product was filtered and washed twice with water (100 mL) to give 2-(hydroxyimino)-N-(o-tolyl)acetamide (95 g, 531 mmol, yield: 76%).

[0102] 1 H-NMR (400MHz, DMSO-d 6 )δ12.16(s,1H),9.47(bs,1H),7.66(s,1H),7.45-7.47(d,J=7.8Hz,1H),7.19-7.24(dd,J=7.4Hz&0.6Hz ,1H),7.14-7.18(td,J=7.6Hz&1.6Hz,1H),7.08-7....

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Abstract

The present invention relates a novel process for preparing a compound of Formula I, wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description. The process comprises a novel and inventive step of converting a dione of Formula II into an isatoic anhydride of Formula V in a single step, wherein R2 is F, Cl, Br or I; R1, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description.

Description

technical field [0001] The present invention relates to a novel process for the preparation of anthranilic diamides, comprising the conversion of isatin to isatoic anhydride. The present invention also relates to a novel process for the preparation of isatoic anhydride which can be used in a process for the preparation of o-carboxamidobenzamides. Background technique [0002] WO2003015518, WO2003015519, WO2004067528, WO2005077934 and WO20100069502 disclose the use of o-carboxamidobenzamide compounds for controlling invertebrate pests such as arthropods. [0003] Some patent documents, such as WO2004011447, WO2004111030, WO2006062978, WO2008010897 and WO2012103436, disclose methods for preparing o-carboxamidobenzamides and suitable intermediates. [0004] However, the methods described in the above documents are laborious or lack sufficient selectivity, and there is still a need to find a simple, efficient and industrially economical method for the preparation of o-carboxami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
CPCC07D401/04C07D231/22A01N43/90A01N43/56C07D231/14C07D403/06C07D409/12
Inventor 亚历山大·克劳泽纳什里坎特·包萨希卜·卡纳瓦德维贾伊·库马尔·萨尔维苏雷什·库马尔·西塔纳尤夫拉·纳夫纳特·卡莱普拉莫德·苏巴斯·纳格尔迪帕克·尚卡尔·潘曼德
Owner PI IND LTD