CN103864701A - Preparation method of 4-sulfanilamide-5-methoxyl-6-chloropyrimidine - Google Patents

Preparation method of 4-sulfanilamide-5-methoxyl-6-chloropyrimidine Download PDF

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CN103864701A
CN103864701A CN201410084410.9A CN201410084410A CN103864701A CN 103864701 A CN103864701 A CN 103864701A CN 201410084410 A CN201410084410 A CN 201410084410A CN 103864701 A CN103864701 A CN 103864701A
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mass parts
sulfanilamide
trieline
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CN103864701B (en
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李涛
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Jiangsu Jinshen Pharmaceutical Technology Co., Ltd
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CHANGSHU JINSHEN MEDICAL CHEMISTRY PRODUCTS Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Processing Of Solid Wastes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention discloses a preparation method of 4-sulfanilamide-5-methoxyl-6-chloropyrimidine. The preparation method comprises the following steps of: (1) chlorination reaction: adding phosphorus oxychloride to a reaction kettle, adding 5-methoxyl-4,6-dihydroxy pyrimidine disodium, carrying out heat-preserving reaction, decompressing to recover phosphorus oxychloride, adding trichloroethylene, adding water, and stirring; separating a trichloroethylene layer, adding trichloroethylene again, repeatedly extracting, discharging, naturally airing, then adding a crude chloride to a refining kettle, adding methanol, heating for dissolution, discharging, and drying to obtain 5-methoxyl-4,6-dichloropyrimidine; (2) condensation reaction: firstly adding dimethyl sulfoxide to a reaction pot, adding 5-methoxyl-4,6-dichloropyrimidine and sulfanilamide sodium, regulating a PH value, compressing into a cooling pot, centrifugalizing sulfanilamide, pumping a mother solution into a decoloring pot, adding active carbon, filtering and separating active carbon, and compressing the mother solution into a crystallizing pot; acidifying, spin-drying a discharged material, drying, and cooling the discharged material to obtain a product. The preparation method disclosed by the invention is high in yield and fewer in by-products and does not damage reaction products.

Description

The preparation method of 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide
Technical field
The invention belongs to chemical drugs intermediate preparing technical field, be specifically related to a kind of preparation method of 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide.
Background technology
4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide is the significant process intermediate of preparing the chemical drugs such as Sulphadoxine.In 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide preparation process, traditional preparation is generally as solvent with dimethyl formamide, but use dimethyl formamide as solvent, there are some following significant shortcomings: after reaction finishes, need to carry out solvent recuperation, recovery time is longer, and temperature drift destroys reaction product, cause by product many, yield is not high.
Therefore, be necessary to be improved for the technology of preparing of existing 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide.
Summary of the invention
The preparation method who the object of the present invention is to provide a kind of 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide, its yield is high, does not destroy reaction product, and by product is less.
For achieving the above object, technical scheme of the present invention is the preparation method of a kind of 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide of design, comprises the steps:
1) chlorination reaction: drop into 650～950 mass parts Phosphorus Oxychlorides in reactor, add 245 mass parts 5-methoxyl group-4,6-dihydroxy pyrimidine disodium, control adds speed, and interior temperature is heated to 80～140 DEG C, insulation reaction 2～6 hours, reclaim under reduced pressure Phosphorus Oxychloride is dry to material, interior temperature is cooled to below 80 DEG C, adds trieline, stirs, put to hydrolyzer, in hydrolyzer, put into 1000～3000 mass parts water, open and stir, controlled hydrolysis temperature≤80 DEG C; Divide and remove trieline layer, then add trieline, extracting 3～7 times repeatedly, trieline layer is put into still pot and is reclaimed trieline, finally controls 80～130 DEG C of distillation temperatures, steam off, blowing, natural air drying, to weight loss on drying≤3%, obtains thick muriate, again thick muriate is dropped into the methyl alcohol that adds 1～5 times of amount in refining kettle, be heated to 50～70 DEG C of dissolvings, be entirely cooled to 0～30 DEG C after molten, discharging, centrifugal rejection filter, discharging is dried, obtain 170～240 mass parts 5-methoxyl group-4,6-dichloro pyrimidine; Wherein, total input amount of trieline is 1000 mass parts;
2) condensation reaction: first 50～100 mass parts dimethyl sulfoxide (DMSO) are dropped in dry reactor, start stirring, drop into 105 mass parts 5-methoxyl group-4, 6-dichloro pyrimidine, 230～300 mass parts sulfanilamide (SN) sodium, be heated to 70～100 DEG C, regulate pH value to 8～10, be incubated 1～4 hour, insulation finishes to add 200～700 mass parts hot water, after all dissolving, be pressed into cooling pan, then add 10%～15% hydrochloric acid, regulate PH to 6～8, be cooled to 5～25 DEG C, centrifugation sulfanilamide (SN), be washed with water to mother liquid coming clear till, dry, by mother liquor suction Decolouring pot, be heated to 50～90 DEG C, add 2 mass parts gacs, decolour 20～40 minutes, filtering separation gac, mother liquor is pressed into crystallizing pan, drip 10%～15% hydrochloric acid acid out at 50～90 DEG C, acid out terminal pH value is 3.0～5.1, then centrifuge dehydration, clarify with hot wash to liquid outlet, dry discharging, in circulation baking oven, 80～130 DEG C are dried, cooling discharging, obtains 140～180 mass parts 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide.
Advantage of the present invention and beneficial effect are: a kind of preparation method of 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide is provided, and its yield is high, does not destroy reaction product, and by product is less.
Embodiment
Below in conjunction with embodiment, the specific embodiment of the present invention is further described.Following examples are only for technical scheme of the present invention is more clearly described, and can not limit the scope of the invention with this.
The concrete technical scheme of implementing of the present invention is:
Embodiment 1
A preparation method for 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide, comprises the steps:
1) chlorination reaction: drop into 650kg Phosphorus Oxychloride in reactor, add 5-methoxyl group-4 of 245kg, 6-dihydroxy pyrimidine disodium, control adds speed, and interior temperature is heated to 80 DEG C, insulation reaction 2 hours, reclaim under reduced pressure Phosphorus Oxychloride is dry to material, interior temperature is cooled to below 80 DEG C, adds trieline, stirs, put to hydrolyzer, in hydrolyzer, put into 1000kg water, open and stir, controlled hydrolysis temperature≤80 DEG C; Divide and remove trieline layer, then add trieline, extracting 3 times repeatedly, trieline layer is put into still pot and is reclaimed trieline, finally controls 80 DEG C of distillation temperatures, steam off, blowing, natural air drying, to weight loss on drying≤3%, obtains thick muriate, again thick muriate is dropped into the methyl alcohol that adds 1 times of amount in refining kettle, be heated to 50 DEG C of dissolvings, be entirely cooled to 0 DEG C after molten, discharging, centrifugal rejection filter, discharging is dried, obtain 5-methoxyl group-4 of 170kg, 6-dichloro pyrimidine; Wherein, total input amount of trieline is 1000kg;
2) condensation reaction: first 50kg dimethyl sulfoxide (DMSO) is dropped in dry reactor, start stirring, drop into 5-methoxyl group-4 of 105kg, 6-dichloro pyrimidine, 230kg sulfanilamide (SN) sodium, be heated to 70 DEG C, regulate pH value to 8, be incubated 1 hour, insulation finishes to add 200kg hot water, after all dissolving, be pressed into cooling pan, then add 10% hydrochloric acid, regulate PH to 6, be cooled to 5 DEG C, centrifugation sulfanilamide (SN), be washed with water to mother liquid coming clear till, dry, by mother liquor suction Decolouring pot, be heated to 50 DEG C, add 2kg gac, decolour 20 minutes, filtering separation gac, mother liquor is pressed into crystallizing pan, drip 10% hydrochloric acid acid out at 50 DEG C, acid out terminal pH value is 3.0, and then centrifuge dehydration is clarified with hot wash to liquid outlet, dries discharging, in circulation baking oven 80 DEG C dry, cooling discharging, obtains 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide of 140kg.
Embodiment 2
A preparation method for 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide, comprises the steps:
1) chlorination reaction: drop into 950kg Phosphorus Oxychloride in reactor, add 5-methoxyl group-4 of 245kg, 6-dihydroxy pyrimidine disodium, control adds speed, and interior temperature is heated to 140 DEG C, insulation reaction 6 hours, reclaim under reduced pressure Phosphorus Oxychloride is dry to material, interior temperature is cooled to below 80 DEG C, adds trieline, stirs, put to hydrolyzer, in hydrolyzer, put into 3000kg water, open and stir, controlled hydrolysis temperature≤80 DEG C; Divide and remove trieline layer, then add trieline, extracting 7 times repeatedly, trieline layer is put into still pot and is reclaimed trieline, finally controls 130 DEG C of distillation temperatures, steam off, blowing, natural air drying, to weight loss on drying≤3%, obtains thick muriate, again thick muriate is dropped into the methyl alcohol that adds 5 times of amounts in refining kettle, be heated to 70 DEG C of dissolvings, be entirely cooled to 30 DEG C after molten, discharging, centrifugal rejection filter, discharging is dried, obtain 5-methoxyl group-4 of 240kg, 6-dichloro pyrimidine; Wherein, total input amount of trieline is 1000kg;
2) condensation reaction: first 50～100kg dimethyl sulfoxide (DMSO) is dropped in dry reactor, start stirring, drop into 5-methoxyl group-4 of 105kg, 6-dichloro pyrimidine, 300kg sulfanilamide (SN) sodium, be heated to 100 DEG C, regulate pH value to 10, be incubated 4 hours, insulation finishes to add 700kg hot water, after all dissolving, be pressed into cooling pan, then add 15% hydrochloric acid, regulate PH to 8, be cooled to 25 DEG C, centrifugation sulfanilamide (SN), be washed with water to mother liquid coming clear till, dry, by mother liquor suction Decolouring pot, be heated to 90 DEG C, add 2kg gac, decolour 40 minutes, filtering separation gac, mother liquor is pressed into crystallizing pan, drip 15% hydrochloric acid acid out at 90 DEG C, acid out terminal pH value is 5.1, and then centrifuge dehydration is clarified with hot wash to liquid outlet, dries discharging, in circulation baking oven 130 DEG C dry, cooling discharging, obtains 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide of 180kg.
Embodiment 3
A preparation method for 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide, comprises the steps:
1) chlorination reaction: drop into 750kg Phosphorus Oxychloride in reactor, add 5-methoxyl group-4 of 245kg, 6-dihydroxy pyrimidine disodium, control adds speed, and interior temperature is heated to 100 DEG C, insulation reaction 4 hours, reclaim under reduced pressure Phosphorus Oxychloride is dry to material, interior temperature is cooled to below 80 DEG C, adds trieline, stirs, put to hydrolyzer, in hydrolyzer, put into 2000kg water, open and stir, controlled hydrolysis temperature≤80 DEG C; Divide and remove trieline layer, then add trieline, extracting 5 times repeatedly, trieline layer is put into still pot and is reclaimed trieline, finally controls 100 DEG C of distillation temperatures, steam off, blowing, natural air drying, to weight loss on drying≤3%, obtains thick muriate, again thick muriate is dropped into the methyl alcohol that adds 3 times of amounts in refining kettle, be heated to 60 DEG C of dissolvings, be entirely cooled to 20 DEG C after molten, discharging, centrifugal rejection filter, discharging is dried, obtain 5-methoxyl group-4 of 200kg, 6-dichloro pyrimidine; Wherein, total input amount of trieline is 1000kg;
2) condensation reaction: first 80kg dimethyl sulfoxide (DMSO) is dropped in dry reactor, start stirring, drop into 5-methoxyl group-4 of 105kg, 6-dichloro pyrimidine, 270kg sulfanilamide (SN) sodium, be heated to 90 DEG C, regulate pH value to 9, be incubated 3 hours, insulation finishes to add 500kg hot water, after all dissolving, be pressed into cooling pan, then add 13% hydrochloric acid, regulate PH to 7, be cooled to 15 DEG C, centrifugation sulfanilamide (SN), be washed with water to mother liquid coming clear till, dry, by mother liquor suction Decolouring pot, be heated to 70 DEG C, add 2kg gac, decolour 30 minutes, filtering separation gac, mother liquor is pressed into crystallizing pan, drip 13% hydrochloric acid acid out at 70 DEG C, acid out terminal pH value is 4.1, and then centrifuge dehydration is clarified with hot wash to liquid outlet, dries discharging, in circulation baking oven 100 DEG C dry, cooling discharging, obtains 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide of 160kg.
 
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, do not departing under the prerequisite of the technology of the present invention principle; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.

Claims (1)

  1. The preparation method of 1.4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide, is characterized in that, comprises the steps:
    1) chlorination reaction: drop into 650～950 mass parts Phosphorus Oxychlorides in reactor, add 245 mass parts 5-methoxyl group-4,6-dihydroxy pyrimidine disodium, interior temperature is heated to 80～140 DEG C, insulation reaction 2～6 hours, reclaim under reduced pressure Phosphorus Oxychloride is dry to material, and interior temperature is cooled to below 80 DEG C, add trieline, stir, put to hydrolyzer, in hydrolyzer, put into 1000～3000 mass parts water, open and stir, controlled hydrolysis temperature≤80 DEG C; Divide and remove trieline layer, then add trieline, extracting 3～7 times repeatedly, trieline layer is put into still pot and is reclaimed trieline, finally controls 80～130 DEG C of distillation temperatures, steam off, blowing, natural air drying, to weight loss on drying≤3%, obtains thick muriate, again thick muriate is dropped into the methyl alcohol that adds 1～5 times of amount in refining kettle, be heated to 50～70 DEG C of dissolvings, be entirely cooled to 0～30 DEG C after molten, discharging, centrifugal rejection filter, discharging is dried, obtain 170～240 mass parts 5-methoxyl group-4,6-dichloro pyrimidine; Wherein, total input amount of trieline is 1000 mass parts;
    2) condensation reaction: first 50～100 mass parts dimethyl sulfoxide (DMSO) are dropped in dry reactor, start stirring, drop into 105 mass parts 5-methoxyl group-4, 6-dichloro pyrimidine, 230～300 mass parts sulfanilamide (SN) sodium, be heated to 70～100 DEG C, regulate pH value to 8～10, be incubated 1～4 hour, insulation finishes to add 200～700 mass parts hot water, after all dissolving, be pressed into cooling pan, then add 10%～15% hydrochloric acid, regulate PH to 6～8, be cooled to 5～25 DEG C, centrifugation sulfanilamide (SN), be washed with water to mother liquid coming clear till, dry, by mother liquor suction Decolouring pot, be heated to 50～90 DEG C, add 2 mass parts gacs, decolour 20～40 minutes, filtering separation gac, mother liquor is pressed into crystallizing pan, drip 10%～15% hydrochloric acid acid out at 50～90 DEG C, acid out terminal pH value is 3.0～5.1, then centrifuge dehydration, clarify with hot wash to liquid outlet, dry discharging, in circulation baking oven, 80～130 DEG C are dried, cooling discharging, obtains 140～180 mass parts 4-sulfanilamide (SN)-5-methoxyl group-6-chloropyrimide.
CN201410084410.9A 2014-03-10 2014-03-10 The preparation method of 4-sulfanilamide-5-methoxyl group-6-chloropyrimide Active CN103864701B (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104370826A (en) * 2014-12-13 2015-02-25 常熟市金申医化制品有限责任公司 Preparation method of 5-methoxyl-4,6-dichloro pyrimidine

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CN1633418A (en) * 2000-09-25 2005-06-29 埃科特莱茵药品有限公司 Arylalkane-sulfonamides having endothelin-antagonist activity
US20090286810A1 (en) * 2008-05-19 2009-11-19 Moore Ii Bob M Pyrimidine Non-Classical Cannabinoid Compounds and Related Methods of Use
CN102219749A (en) * 2010-04-14 2011-10-19 上海京新生物医药有限公司 Method for preparing rosuvastatin calcium
CN102304094A (en) * 2011-09-23 2012-01-04 常熟市南湖实业化工有限公司 Preparation method of sulfadoxine and intermediate thereof
CN102311393A (en) * 2011-09-23 2012-01-11 常熟市金申医化制品有限责任公司 Preparation method of sulfadoxine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1633418A (en) * 2000-09-25 2005-06-29 埃科特莱茵药品有限公司 Arylalkane-sulfonamides having endothelin-antagonist activity
US20090286810A1 (en) * 2008-05-19 2009-11-19 Moore Ii Bob M Pyrimidine Non-Classical Cannabinoid Compounds and Related Methods of Use
CN102219749A (en) * 2010-04-14 2011-10-19 上海京新生物医药有限公司 Method for preparing rosuvastatin calcium
CN102304094A (en) * 2011-09-23 2012-01-04 常熟市南湖实业化工有限公司 Preparation method of sulfadoxine and intermediate thereof
CN102311393A (en) * 2011-09-23 2012-01-11 常熟市金申医化制品有限责任公司 Preparation method of sulfadoxine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104370826A (en) * 2014-12-13 2015-02-25 常熟市金申医化制品有限责任公司 Preparation method of 5-methoxyl-4,6-dichloro pyrimidine
CN104370826B (en) * 2014-12-13 2017-01-11 常熟市金申医化制品有限责任公司 Preparation method of 5-methoxyl-4,6-dichloro pyrimidine

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