DE1695865C - Process for the preparation of 4-sufanilamido-2,6-dimethoxy-pyrimidine of a high degree of purity - Google Patents
Process for the preparation of 4-sufanilamido-2,6-dimethoxy-pyrimidine of a high degree of purityInfo
- Publication number
- DE1695865C DE1695865C DE19671695865 DE1695865A DE1695865C DE 1695865 C DE1695865 C DE 1695865C DE 19671695865 DE19671695865 DE 19671695865 DE 1695865 A DE1695865 A DE 1695865A DE 1695865 C DE1695865 C DE 1695865C
- Authority
- DE
- Germany
- Prior art keywords
- sulfanilamido
- dimethoxypyrimidine
- weight
- parts
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 159000000000 sodium salts Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- ZZORFUFYDOWNEF-UHFFFAOYSA-N Sulfadimethoxine Chemical class COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- LNTJJKHTAZFVJJ-UHFFFAOYSA-N 2,6-dimethoxypyrimidin-4-amine Chemical compound COC1=CC(N)=NC(OC)=N1 LNTJJKHTAZFVJJ-UHFFFAOYSA-N 0.000 claims description 3
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkali metal salts Chemical class 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 2
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims 7
- 238000005185 salting out Methods 0.000 claims 6
- 238000009833 condensation Methods 0.000 claims 4
- 230000005494 condensation Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000007859 condensation product Substances 0.000 claims 3
- 238000003381 deacetylation reaction Methods 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- 238000007127 saponification reaction Methods 0.000 claims 3
- KEVRHVMWBKFGLO-UHFFFAOYSA-N 2,4-dimethoxypyrimidine Chemical compound COC1=CC=NC(OC)=N1 KEVRHVMWBKFGLO-UHFFFAOYSA-N 0.000 claims 2
- YLZYSVYZMDJYOT-UHFFFAOYSA-N 2-methoxypyrimidine Chemical compound COC1=NC=CC=N1 YLZYSVYZMDJYOT-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 102100009854 MID1 Human genes 0.000 claims 2
- 101700079340 MID1 Proteins 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- FPSPPRZKBUVEJQ-UHFFFAOYSA-N 4,6-dimethoxypyrimidine Chemical compound COC1=CC(OC)=NC=N1 FPSPPRZKBUVEJQ-UHFFFAOYSA-N 0.000 claims 1
- HQUSMHJZQKEXHO-UHFFFAOYSA-N 4-amino-N-(2-methoxypyrimidin-4-yl)benzenesulfonamide Chemical compound COC1=NC=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 HQUSMHJZQKEXHO-UHFFFAOYSA-N 0.000 claims 1
- 150000005007 4-aminopyrimidines Chemical class 0.000 claims 1
- FZERHIULMFGESH-UHFFFAOYSA-N Acetanilide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 1
- 102100017602 DEGS1 Human genes 0.000 claims 1
- 101700014831 DEGS1 Proteins 0.000 claims 1
- 230000036826 Excretion Effects 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000005712 crystallization Effects 0.000 claims 1
- 238000004042 decolorization Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
- 230000001131 transforming Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 241000690470 Plantago princeps Species 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
Description
20 Gewichtsteile reinen, farblosen 4-Sulfanil-20 parts by weight of pure, colorless 4-sulfanil
83,4 °/o der theoretischen, bezogen auf das eingesetzte 4-Amino-2,6-diraethoxypyrimidin. a83.4% of the theoretical, based on the amount used 4-amino-2,6-diraethoxypyrimidine. a
12 Gewichtsteile 4-Amino-2,6-dimethoxypyrimidin werden entsprechend Beispiel 1 mit 20 Gewichtsteilen p-Acetylaminobenzolsulfochlorid kondensiert. Der Rückstand wird nach Abdestillieren des Pyridine in 150 Gewichtsteilen 8°/oiger wäßriger Natriumhydroxydlösung aufgenonunen und drei Stunden lang auf eine Temperatur von 70 bis 800C erwärmt. Gleichzeitig werden unter vermindertem Druck 50 Gev/ichtsteile des Azeotrops Wasser—Pyridin abdestilliert. Die Lösung wird auf 50 bis 6O0C abgekühlt, mit Aktivkohle entfärbt, filtriert und weiter bis auf 5°C gekühlt. Bei dieser Temperatur scheiden sich die ersten Kristalle des Natriumsalzes des 4-Sulfanilamido-2,6-dimethoxypyrimidine aus. Nach einiger Zeit wird die Temperatur bis auf 00C herabgesetzt, und der Rest des vorgenannten Natriumsalzes wird durch Zugabe von 10 bis 15 Gewichtsteilen 40ο/ο·8βΓ Natriumhydroxydlösung ausgesalzen. Das abgesaugte Natriumsalz des 4-Sulfanil- aj amido-2,6-dimethoxypyrimidins wird bei einer Temperatur etwa um O0C mit gesättigter Natriumchloridlösung gewaschen, und nach Beispiel 1 aufgearbeitet. Man erhält so 19,6 Gewichtsteüe von farblosem, StrAÄnen^n bezug auf das eingesetZte ^Amino-^ö-dimethoxypyrimidm.12 parts by weight of 4-amino-2,6-dimethoxypyrimidine are condensed according to Example 1 with 20 parts by weight of p-acetylaminobenzene sulfochloride. The residue is aufgenonunen after distilling off the pyridine in 150 parts by weight of 8 ° / o aqueous sodium hydroxide solution and heated for three hours at a temperature of 70 to 80 0 C. At the same time, 50 parts by weight of the azeotrope water-pyridine are distilled off under reduced pressure. The solution is cooled to 50 to 6O 0 C, decolorized with charcoal, filtered and continue until cooled to 5 ° C. At this temperature, the first crystals of the sodium salt of 4-sulfanilamido-2,6-dimethoxypyrimidine separate out. After some time the temperature is reduced to 0 0 C, and the rest of the aforesaid sodium salt is salted out by adding 10 to 15 parts 40 ο / ο · 8βΓ sodium hydroxide solution. The sucked off sodium salt of 4-sulfanil-aj amido-2,6-dimethoxypyrimidine is washed with saturated sodium chloride solution at a temperature of about 0 ° C. and worked up according to example 1. Thus obtained 19.6 Gewichtsteüe colorless, StrAÄnen ^ n respect to the eingese tZ te ^ ^ ö amino-dimethoxypyrimidm.
Beispiel 3 12Gewichtsteile ^Amino^ö-dimethoxypyrimidinExample 3 12 parts by weight of ^ amino ^ δ-dimethoxypyrimidine
werden e««!P^.^^SSSSSS p-AcetylammobenzolsunocnJona be e ««! P ^. ^^ SSSSSS p-AcetylammobenzolsunocnJona
seift.soaps.
Die Temperatur
Losung wird ratThe temperature
The solution is advice
Nach ^
unterAfter ^
under
50oC herabgesetzt, die entfärbt und filtriert. Reduced to 50 o C , which discolors and filters.
ichteteile Natrium^ Natriumsalz Partial sodium salt
xypyrimidins wird ypy 5oc xypyrimidins becomes ypy 5oc
des ^Sulfanilarnido^des ^ sulfanilarnido ^
nacht Abkuhkn der M^chung ^ „^ ω after t kuhkn the M ^ chung ^ "^ ω
saugt und^™^fsa^he ·„ m Gewichtsteiien sucks and ^ ™ ^ f sa ^ he · „ m weight steiien
^ε5εΓ ρ7^ι und mit Aktivkohle entfärbt. Aus Wasser^ gelost ^and mit Ale fanilamido.2i6.di.^ ε5εΓ ρ 7 ^ ι and decolorized with activated charcoal. Dissolved from water and with ale fanilamido. 2i6 . di .
die er Losung wird Cas^r^ { Salzsäure aufthe solution is made up of Cas ^ r ^ { hydrochloric acid
^^tw^^nt. abfiltriert und Man erhält so 18,8 Gewichtsbezug auf das^^ tw ^^ nt. filtered off and This gives 18.8 weight reference to the
^kt von200bis202°C. 78>3«/0 der theoretischen in , £Amino_2)6_dimethoxy-^ kt from 200 to 202 ° C. 78> 3 "/ 0 of the theoretical in, £ amino _ 2) 6 _ dim ethoxy-
Claims (2)
2,6-dimethoxypyrimidins, das dadurch gekennzeichnet . · 1 1The invention relates to a process for the preparation of 4-sulfanilamido-2,6-dimethoxypyrimidine, a subsequent decoloration with activated charcoal and known therapeutically effective agent, by acidifying with hydrochloric acid up to a pH value of 6, in water until condensation of 4-amino-2,6-dimethoxypyrimidine 6.5 results in completely colorless 4-sulfanilamido-2,6-dimit p-acetylaminobenzene sulfochloride, saponification of methoxypyrimidine. The yield of this process of condensation product with aqueous sodium hydroxide is 80 to 85%, based on 4-amino-2,6-dixide solution and isolation of the pure 4-sulfanilamido methoxypyrimidine.
2,6-dimethoxypyrimidine, which is characterized. 1 1
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL116091A PL58169B1 (en) | 1966-08-15 | ||
PL11609166 | 1966-08-15 | ||
PL12104167 | 1967-06-09 | ||
PL121041A PL57901B1 (en) | 1967-06-09 | ||
DEST027252 | 1967-08-16 |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1695865A1 DE1695865A1 (en) | 1972-03-16 |
DE1695865B2 DE1695865B2 (en) | 1973-01-11 |
DE1695865C true DE1695865C (en) | 1973-08-09 |
Family
ID=
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