DK175638B1 - Fremgangsmåde til syntese af arylsulfonylalkylamider - Google Patents
Fremgangsmåde til syntese af arylsulfonylalkylamider Download PDFInfo
- Publication number
- DK175638B1 DK175638B1 DK198901279A DK127989A DK175638B1 DK 175638 B1 DK175638 B1 DK 175638B1 DK 198901279 A DK198901279 A DK 198901279A DK 127989 A DK127989 A DK 127989A DK 175638 B1 DK175638 B1 DK 175638B1
- Authority
- DK
- Denmark
- Prior art keywords
- alkylamine
- alkaline agent
- excess
- moles
- organic phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000012074 organic phase Substances 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-Butylbenzenesulfonamide Natural products CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 9
- 239000004014 plasticizer Substances 0.000 abstract description 5
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- -1 arylsulphonyl halide Chemical class 0.000 abstract 2
- 239000000047 product Substances 0.000 description 17
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- 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
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polyamides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8803447A FR2628739B1 (fr) | 1988-03-17 | 1988-03-17 | Procede de synthese d'arylsulfonylalkylamide |
| FR8803447 | 1988-03-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK127989D0 DK127989D0 (da) | 1989-03-16 |
| DK127989A DK127989A (da) | 1989-09-18 |
| DK175638B1 true DK175638B1 (da) | 2005-01-03 |
Family
ID=9364346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198901279A DK175638B1 (da) | 1988-03-17 | 1989-03-16 | Fremgangsmåde til syntese af arylsulfonylalkylamider |
Country Status (14)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3176619B2 (ja) * | 1991-09-05 | 2001-06-18 | ファルノ−ヴェトロファルム ゲゼルシャフト ミット ベシュレンクテル ハフツング | 芳香族スルホンアミド化合物、阻害剤及びそれを含有する医薬組成物 |
| TW219358B (enrdf_load_stackoverflow) * | 1991-12-20 | 1994-01-21 | Hokuriku Pharmaceutical | |
| GB9625781D0 (en) * | 1996-12-11 | 1997-01-29 | Zeneca Ltd | Chemical process |
| JP5076682B2 (ja) * | 2006-07-26 | 2012-11-21 | セントラル硝子株式会社 | Ｎ−（ビシクロ［２，２，１］ヘプト−５−エン−２−イルメチル）−１，１，１−トリフルオロメタンスルホンアミドの製造方法 |
| CN109369473A (zh) * | 2018-09-19 | 2019-02-22 | 南通沃兰化工有限公司 | 一种n-丁基苯磺酰胺的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833650A1 (de) * | 1978-08-01 | 1980-02-21 | Basf Ag | Verfahren zur herstellung thermostabiler arylsulfonylalkylamide |
| DE2941593A1 (de) * | 1979-10-13 | 1981-04-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von sulfonamiden |
-
1988
- 1988-03-17 FR FR8803447A patent/FR2628739B1/fr not_active Expired - Lifetime
-
1989
- 1989-02-20 CA CA000591539A patent/CA1307295C/fr not_active Expired - Lifetime
- 1989-03-01 NO NO890864A patent/NO170412C/no not_active IP Right Cessation
- 1989-03-07 DE DE68912797T patent/DE68912797T2/de not_active Expired - Lifetime
- 1989-03-07 EP EP89400638A patent/EP0333557B1/fr not_active Expired - Lifetime
- 1989-03-07 ES ES89400638T patent/ES2062055T3/es not_active Expired - Lifetime
- 1989-03-07 AT AT89400638T patent/ATE101129T1/de not_active IP Right Cessation
- 1989-03-15 JP JP1063399A patent/JPH024766A/ja active Granted
- 1989-03-16 FI FI891256A patent/FI90763C/fi not_active IP Right Cessation
- 1989-03-16 IE IE85889A patent/IE63494B1/en not_active IP Right Cessation
- 1989-03-16 DK DK198901279A patent/DK175638B1/da not_active IP Right Cessation
- 1989-03-16 PT PT90025A patent/PT90025B/pt not_active IP Right Cessation
- 1989-03-17 KR KR1019890003358A patent/KR940010765B1/ko not_active Expired - Lifetime
- 1989-03-17 CN CN89101437A patent/CN1020600C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR940010765B1 (ko) | 1994-11-11 |
| FR2628739B1 (fr) | 1990-09-07 |
| CN1020600C (zh) | 1993-05-12 |
| FR2628739A1 (fr) | 1989-09-22 |
| IE63494B1 (en) | 1995-05-03 |
| FI90763B (fi) | 1993-12-15 |
| DE68912797D1 (de) | 1994-03-17 |
| FI891256A0 (fi) | 1989-03-16 |
| NO170412C (no) | 1992-10-14 |
| EP0333557A3 (en) | 1990-10-17 |
| IE890858L (en) | 1989-09-17 |
| DK127989A (da) | 1989-09-18 |
| NO890864D0 (no) | 1989-03-01 |
| JPH024766A (ja) | 1990-01-09 |
| CN1037894A (zh) | 1989-12-13 |
| DE68912797T2 (de) | 1994-06-01 |
| ATE101129T1 (de) | 1994-02-15 |
| PT90025A (pt) | 1989-11-10 |
| CA1307295C (fr) | 1992-09-08 |
| PT90025B (pt) | 1994-05-31 |
| NO890864L (no) | 1989-09-18 |
| JPH0465063B2 (enrdf_load_stackoverflow) | 1992-10-16 |
| KR890014464A (ko) | 1989-10-23 |
| EP0333557A2 (fr) | 1989-09-20 |
| FI891256L (fi) | 1989-09-18 |
| EP0333557B1 (fr) | 1994-02-02 |
| DK127989D0 (da) | 1989-03-16 |
| NO170412B (no) | 1992-07-06 |
| FI90763C (fi) | 1994-03-25 |
| ES2062055T3 (es) | 1994-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |