CN106905180A - The synthetic method of photosensitive material stabilizer neighbour's hexyl certain herbaceous plants with big flowers base oxybenzamide - Google Patents
The synthetic method of photosensitive material stabilizer neighbour's hexyl certain herbaceous plants with big flowers base oxybenzamide Download PDFInfo
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- CN106905180A CN106905180A CN201710093506.5A CN201710093506A CN106905180A CN 106905180 A CN106905180 A CN 106905180A CN 201710093506 A CN201710093506 A CN 201710093506A CN 106905180 A CN106905180 A CN 106905180A
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- Prior art keywords
- oxybenzamide
- herbaceous plants
- big flowers
- certain herbaceous
- flowers base
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the synthesis technique of photosensitive material stabilizer neighbour's hexyl certain herbaceous plants with big flowers base oxybenzamide.With different hexadecanol as raw material, with the benzene sulfonyl chloride reaction different hexadecanol phenylbenzimidazole sulfonic acid ester of generation in the presence of acid binding agent, further there is substitution reaction and obtain adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide in product with salicylamide in the basic conditions without purifying.The influence of influence and alkali that acid binding agent produces to hexadecanol phenylbenzimidazole sulfonic acid ester to salicylamide substitution reaction has been investigated, a simple to operate, economic and practical technique has been have found.
Description
Technical field
The invention belongs to a kind of photosensitive material stabilizer neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide in compound synthesis field
Preparation method.
Background technology
Current most photographic silver halide technique is all based on anti-between photosensitizing dye colour coupler and oxidized developing agent
Should.Photosensitive material colour coupler light resistance and heat endurance be not high, even if being stored in dark place, it is also possible to chemically react, because
Add appropriate stabilizer in this gelatin to photosensitizing dye colour coupler, the anti-oxidant and light that can improve photosensitive material colour coupler is steady
It is set for using.Alkoxy benzamides are a kind of new photosensitive material stabilizers, can be sufficiently mixed with photosensitive material colour coupler
Together, with fine particles even distribution in the gelatin of photosensitizing dye colour coupler, turbidity very little, transparency is very high.Alkoxy
The application of benzamide market can be more and more extensive.
Adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide is the pigment image stabilizing agent in a kind of new photosensitive material, is prepared at present
There is product poor transparency in the method for adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide, the shortcoming that purity is not high and yield is low.
The content of the invention
It is an object of the invention to overcome the deficiencies in the prior art part, there is provided a kind of photosensitive material stabilizer neighbour hexyl certain herbaceous plants with big flowers
The preparation method of base oxybenzamide.The invention provides the reaction scheme of simple and fast, catalyst, reaction temperature, reaction
Material ratio, thus provides a kind of lower photosensitive material stabilizer neighbour's hexyl certain herbaceous plants with big flowers base oxybenzamide of more practical, cost
Production technology.
The present invention solves its technical problem and takes following technical scheme to realize：
A kind of synthetic method of photosensitive material stabilizer neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, intermediate is different hexadecanol benzene
Base sulphonic acid ester, the structural formula for being related to intermediate and product is：
Preferably, it is raw material to use different hexadecanol, with phenylsulfonylchloride reaction generation different 16 in the presence of acid binding agent
, further there is substitution reaction with salicylamide in the basic conditions and obtain adjacent hexyl certain herbaceous plants with big flowers base epoxide benzoyl in alcohol phenylbenzimidazole sulfonic acid ester
Amine.
Preferably, the solvent for being used in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is toluene and dichloromethane；Adjacent hexyl certain herbaceous plants with big flowers
The solvent used in the production of base oxybenzamide is N,N-dimethylformamide and dimethyl sulfoxide.
Preferably, using acid binding agent it is Anhydrous potassium carbonate and triethylamine in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester；It is adjacent oneself
The alkali used in the production of base certain herbaceous plants with big flowers base oxybenzamide is natrium carbonicum calcinatum and Anhydrous potassium carbonate.
Preferably, the amount ratio of the material of the material in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is：Different hexadecanol：Methyl sulphur
Acyl chlorides：Acid binding agent=1:1.05:1.05；The amount ratio of the material of the material in the production of adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide is：
Different hexadecanol phenylbenzimidazole sulfonic acid ester：Alkali：Salicylamide=1.05:1.05:1.
Preferably, the reaction temperature in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is 10-15 DEG C；Adjacent hexyl certain herbaceous plants with big flowers base epoxide benzene
Reaction temperature in the production of formamide is 80-100 DEG C.
Preferably, different hexadecanol phenylbenzimidazole sulfonic acid ester directly replaces in the presence of alkali without purifying with salicylamide
Reaction obtains adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide.
Preferably, the purifying of adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide is recrystallized using petroleum ether.
Advantages and positive effects of the present invention are：
1st, the present invention generates different hexadecanol in the presence of acid binding agent with different hexadecanol as raw material with phenylsulfonylchloride reaction
, further there is substitution reaction with salicylamide in the basic conditions and obtain adjacent hexyl certain herbaceous plants with big flowers base epoxide benzoyl in phenylbenzimidazole sulfonic acid ester
Amine.
2nd, the different hexadecanol phenylbenzimidazole sulfonic acid ester of reaction intermediate of the present invention without purifying, directly in the presence of alkali with salicyloyl
Amine reaction obtains adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide.The synthetic method is a technique simple to operate, economic and practical.
Specific embodiment
With reference to specific embodiment, the invention will be further described.The present invention prepares photosensitive material stabilizer neighbour's hexyl
The synthesis chemical formula of certain herbaceous plants with big flowers base oxybenzamide is as follows：
The present invention is described in further detail with reference to embodiment.
Embodiment 1
(1) the different hexadecanols of addition 242kg, 145kg Anhydrous potassium carbonates and 1500 kilograms in 3000 liters of enamel reaction still
Toluene, is cooled in less than 10 DEG C, and 185kg phenylsulfonylchlorides are added dropwise in batches, and reaction 2 hours is continued at 10-15 DEG C after adding, natural
It is increased to and reacts 2 hours at room temperature, stop reaction, add 500 kg of water, stir 1 hour, stratification, removes water layer, it is organic
Through drying, filtering, precipitation obtains different hexadecanol methanesulfonate ester, and the content of product is directly used in next step 95% or so
Reaction.
(2) 137 kilograms of salicylamides of addition, 145 kilograms of natrium carbonicum calcinatums and 800 kilograms in 2000 liters of enamel reaction stills
Dimethyl sulfoxide, is added dropwise the different hexadecanol phenylbenzimidazole sulfonic acid esters of 420kg of previous step production, and 4 are reacted at 80-100 DEG C is warming up to after dripping off
Hour, stop reaction, room temperature is cooled to, 800 kg of water are added, extracted with 800 kilograms of dichloromethane, remove a layer organic phase washing
Once, stand, remove water layer, organic layer obtains crude product through drying, filtering after precipitation, crude product petroleum ether is recrystallized
To 322kg, yield is 89.2%.
Embodiment 2
(1) 363 kilograms of different hexadecanols, 278 kilograms of phenylsulfonylchlorides and 1500 are added in 3000 liters of enamel reaction still
Kilogram dichloromethane, is cooled in less than 10 DEG C, and 160 kilograms of triethylamines are added dropwise, and continues at 10-15 DEG C to react 2 hours after dripping off, from
So it is increased to and reacts 2 hours at room temperature, stop reaction, filtering, removing dichloromethane obtains crude product, and the content of product is 95%
Left and right, for next step reaction.
(2) 185 kilograms of salicylamides of addition, 207 kilograms of Anhydrous potassium carbonates and 800 kilograms in 2000 liters of enamel reaction stills
DMF, is added dropwise the different hexadecanol methanesulfonate ester of previous step production, anti-at 80-100 DEG C is warming up to after dripping off
Answer 4 hours, stop reaction, be cooled to room temperature, add 800 kg of water, extracted with 800 kilograms of dichloromethane, remove a layer organic phase
Washing once, stands, and removes water layer, and organic layer obtains crude product through drying, filtering after precipitation, crude product petroleum ether is tied again
Crystalline substance obtains 492kg, and yield is 90.9%.
Presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, it is all in essence of the invention
Within god and principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.
Claims (8)
1. the synthetic method of a kind of photosensitive material stabilizer neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is characterised in that：Intermediate is
Different hexadecanol phenylbenzimidazole sulfonic acid ester, the structural formula for being related to intermediate and product is：
2. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：It is raw material to use different hexadecanol, with the phenylsulfonylchloride reaction different hexadecanol phenyl sulphur of generation in the presence of acid binding agent
, further there is substitution reaction with salicylamide in the basic conditions and obtain adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide in acid esters.
3. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：The solvent used in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is toluene and dichloromethane；Adjacent hexyl certain herbaceous plants with big flowers base epoxide benzene
The solvent used in the production of formamide is N,N-dimethylformamide and dimethyl sulfoxide.
4. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：Using acid binding agent it is Anhydrous potassium carbonate and triethylamine in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester；Adjacent hexyl certain herbaceous plants with big flowers base oxygen
The alkali used in the production of yl-benzamide is natrium carbonicum calcinatum and Anhydrous potassium carbonate.
5. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：The amount ratio of the material of the material in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is：Different hexadecanol：Methylsufonyl chloride：Tie up
Sour agent=1:1.05:1.05；The amount ratio of the material of the material in the production of adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide is：Different hexadecanol
Phenylbenzimidazole sulfonic acid ester：Alkali：Salicylamide=1.05:1.05:1.
6. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：Reaction temperature in the production of different hexadecanol phenylbenzimidazole sulfonic acid ester is 10-15 DEG C；Adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide
Reaction temperature in production is 80-100 DEG C.
7. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：Different hexadecanol phenylbenzimidazole sulfonic acid ester is directly obtained in the presence of alkali without purifying with salicylamide generation substitution reaction
Adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide.
8. the synthetic method of photosensitive material stabilizer according to claim 1 neighbour hexyl certain herbaceous plants with big flowers base oxybenzamide, it is special
Levy and be：The purifying of adjacent hexyl certain herbaceous plants with big flowers base oxybenzamide is recrystallized using petroleum ether.
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| CN201710093506.5A CN106905180A (en) | 2017-02-21 | 2017-02-21 | The synthetic method of photosensitive material stabilizer neighbour's hexyl certain herbaceous plants with big flowers base oxybenzamide |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101037394A (en) * | 2006-03-16 | 2007-09-19 | 上海佰伦精细化工有限公司 | Preparation method of alkoxy benzamides |
| US20090246815A1 (en) * | 2008-03-31 | 2009-10-01 | Sadanobu Shuto | Protease detection material, set of protease detection materials, and method for measuring protease |
-
2017
- 2017-02-21 CN CN201710093506.5A patent/CN106905180A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101037394A (en) * | 2006-03-16 | 2007-09-19 | 上海佰伦精细化工有限公司 | Preparation method of alkoxy benzamides |
| US20090246815A1 (en) * | 2008-03-31 | 2009-10-01 | Sadanobu Shuto | Protease detection material, set of protease detection materials, and method for measuring protease |
Non-Patent Citations (1)
| Title |
|---|
| R. CASSANO ET AL.: ""The synthesis of new liquid–crystalline mesogens containing bicyclohexane units"", 《TETRAHEDRON LETTERS》 * |
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