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Preparing process of propane diamide compound

A technology of malonamide and compound, applied in the field of preparation of malonamide compounds, can solve the problems of high reaction temperature, long reaction time, long reaction time and the like

Inactive Publication Date: 2004-09-01
CHINA LUCKY FILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former method needs to prepare malonyl chloride with acid chlorination agents such as thionyl chloride, which not only has a long reaction time, but also is highly corrosive, and is generally not suitable for use due to natural conditions such as air humidity. Higher reaction temperature, longer reaction time, lower yield

Method used

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  • Preparing process of propane diamide compound
  • Preparing process of propane diamide compound
  • Preparing process of propane diamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of compound (1)'

[0026]

[0027] Add 170g of 4-chloro-3-amino-dodecyl benzoate, 26g of malonic acid and 1000ml of benzene into a 2000ml three-neck flask, heat to 60°C, add 37.5ml of phosphorus trichloride dropwise within half an hour, and continue The reaction was carried out at this temperature for 1.5 hours, and the benzene solvent was distilled off to obtain 183 g of a white solid with a yield of 98% and a melting point of 94-96°C.

[0028] In the case of other reaction conditions being the same, the temperature was controlled at 62°C and 65°C respectively, and the above compounds were synthesized, and the obtained results were the same.

[0029] C

Embodiment 2

[0031] Synthesis of compound (2)'

[0032] Add 24.9g of n-octyl m-amino-benzoate, 5.2g of malonic acid and 150ml of chlorobenzene into a 500ml three-neck flask, heat to 62°C, add 5.2ml of phosphorus trichloride dropwise within 1 hour, and continue the reaction for 2.0 After 1 hour, the chlorobenzene solvent was distilled off to obtain 26.9 g of a white solid with a yield of 95% and a melting point of 72-75°C.

[0033] In the case of other reaction conditions being the same, the temperature was controlled at 60°C and 65°C respectively, and the above compounds were synthesized, and the obtained results were the same.

[0034] C

Embodiment 3

[0036] Synthesis of compound (3)'

[0037] Add 41.1g of 4-chloro-3-amino-benzoic acid (α-dodecyl methyl acetate), 5.2g of malonic acid and 180ml of benzene into a 500ml three-necked flask, heat to 65°C, and add 5.2ml dropwise within 1 hour After the addition of phosphorus trichloride, the reaction was continued for 1.5 hours, and the benzene solvent was evaporated to obtain 40 g of a white solid with a yield of 90% and a melting point of 66-67°C.

[0038] In the case of other reaction conditions being the same, the temperature was controlled at 60°C and 63°C respectively, and the above compounds were synthesized, and the results obtained were the same.

[0039] C

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Abstract

The present invention provides the preparation process of propane diamide compound. The propane diamide compound is prepared through adding malonic acid, amine and solvent, heating to 60-65 deg.c dropping phosphor trichloride and reaction at the said temperature for 1.5-2 hr. The general reaction expression is 2RNH2+HOOCCH2COOH+PCl3-R-NHCOCH2COLNH-R+H3PO3+HCl. The preparation process of present invention has short reaction period, low reaction temperature and high yield. The propane diamide compound product can be used to release compound parent substance for development inhibitor and development promoter.

Description

technical field [0001] The invention relates to a preparation method of a malonamide compound, in particular to a preparation method of a malonamide compound used in a photographic development inhibitor release compound matrix and a development accelerator release compound matrix. technical background [0002] As everyone knows, in the photographic functional compound, there is a class of compounds that are based on malonamide compounds, and their parent structure can be represented by the following general formula (I): [0003] R-NHCOCH 2 CONH-R [0004] (I) [0005] The compound represented by the general formula (I) is generally prepared by reacting malonyl chloride with an acid chloride such as thionyl chloride, and then reacting malonyl chloride with an aromatic amine or an alkylamine in two steps; or as in the U.S. As described in the patent US4095984, it is prepared by exchange reaction between diethyl malonate and arylam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/02C07C233/07C07C233/15C07C233/25C07C233/54C07C237/22
Inventor 张尚湖马礼谦
Owner CHINA LUCKY FILM CORP
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