DE1259872B - Verfahren zur Herstellung von Sulfonylurethanen bzw. deren Salzen - Google Patents
Verfahren zur Herstellung von Sulfonylurethanen bzw. deren SalzenInfo
- Publication number
- DE1259872B DE1259872B DENDAT1259872D DE1259872DA DE1259872B DE 1259872 B DE1259872 B DE 1259872B DE NDAT1259872 D DENDAT1259872 D DE NDAT1259872D DE 1259872D A DE1259872D A DE 1259872DA DE 1259872 B DE1259872 B DE 1259872B
- Authority
- DE
- Germany
- Prior art keywords
- urethane
- theory
- melting point
- sodium
- yield
- 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.)
- Pending
Links
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 12
- 229940124530 sulfonamide Drugs 0.000 claims description 12
- 150000003456 sulfonamides Chemical class 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- -1 alkaline earth metal salts Chemical class 0.000 description 33
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 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 7
- 239000000203 mixture Substances 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 6
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- YDPWVAMKZSUTGO-UHFFFAOYSA-N benzenesulfonamide;sodium Chemical compound [Na].NS(=O)(=O)C1=CC=CC=C1 YDPWVAMKZSUTGO-UHFFFAOYSA-N 0.000 description 2
- KNZCDDKOBQQVDD-UHFFFAOYSA-N calcium;4-methylbenzenesulfonamide Chemical compound [Ca].CC1=CC=C(S(N)(=O)=O)C=C1 KNZCDDKOBQQVDD-UHFFFAOYSA-N 0.000 description 2
- FECLNUMYMPXVAI-UHFFFAOYSA-N ethyl N-[2-(4-methylphenyl)sulfonylethyl]carbamate Chemical compound CCOC(=O)NCCS(=O)(=O)C1=CC=C(C)C=C1 FECLNUMYMPXVAI-UHFFFAOYSA-N 0.000 description 2
- VHBXLZJBCODOOU-UHFFFAOYSA-N ethyl n-(2-sulfonylethyl)carbamate Chemical compound CCOC(=O)NCC=S(=O)=O VHBXLZJBCODOOU-UHFFFAOYSA-N 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VTLHPYXKUOESEM-UHFFFAOYSA-N sodium;(4-methylphenyl)sulfonylazanide Chemical compound [Na+].CC1=CC=C(S([NH-])(=O)=O)C=C1 VTLHPYXKUOESEM-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- JAZIZPAWJQOERJ-UHFFFAOYSA-N 4-chlorobenzenesulfonamide;sodium Chemical compound [Na].NS(=O)(=O)C1=CC=C(Cl)C=C1 JAZIZPAWJQOERJ-UHFFFAOYSA-N 0.000 description 1
- MWDFYPDSWMARNT-UHFFFAOYSA-N 4-ethyl-3-nitrobenzenesulfonamide Chemical compound CCC1=CC=C(S(N)(=O)=O)C=C1[N+]([O-])=O MWDFYPDSWMARNT-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- JBJYRLLCKMAPCW-UHFFFAOYSA-N C(C)(=O)NC=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC Chemical compound C(C)(=O)NC=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC JBJYRLLCKMAPCW-UHFFFAOYSA-N 0.000 description 1
- QWWOJXLGSSGJKU-UHFFFAOYSA-N C(C)C1=C(C=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC)[N+](=O)[O-] Chemical compound C(C)C1=C(C=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC)[N+](=O)[O-] QWWOJXLGSSGJKU-UHFFFAOYSA-N 0.000 description 1
- BVQHWQVQXJFZLW-UHFFFAOYSA-N C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)OC Chemical compound C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)OC BVQHWQVQXJFZLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NENBAISIHCWPKP-UHFFFAOYSA-N Clofenamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NENBAISIHCWPKP-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- ZBFTYTIYDSKKMF-UHFFFAOYSA-N [K].COc1ccc(cc1OC)S(N)(=O)=O Chemical compound [K].COc1ccc(cc1OC)S(N)(=O)=O ZBFTYTIYDSKKMF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HWCQNZGRHUPEBP-UHFFFAOYSA-N ethyl N-(3,4-dimethoxyphenyl)sulfonyl-N-methylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC(OC)=C(OC)C=C1 HWCQNZGRHUPEBP-UHFFFAOYSA-N 0.000 description 1
- XKBDLAIPLDQGFM-UHFFFAOYSA-N ethyl N-ethyl-N-(4-methoxy-3-nitrophenyl)sulfonylcarbamate Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1OC)S(=O)(=O)N(C(=O)OCC)CC XKBDLAIPLDQGFM-UHFFFAOYSA-N 0.000 description 1
- BZSZSGLQJIWVGD-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)sulfonyl-n-ethylcarbamate Chemical compound CCOC(=O)N(CC)S(=O)(=O)C1=CC=C(Cl)C=C1 BZSZSGLQJIWVGD-UHFFFAOYSA-N 0.000 description 1
- PKGNFJLDVFEWKR-UHFFFAOYSA-N ethyl n-ethyl-n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(CC)S(=O)(=O)C1=CC=C(C)C=C1 PKGNFJLDVFEWKR-UHFFFAOYSA-N 0.000 description 1
- CXLBYPJSAWOYSI-UHFFFAOYSA-N ethyl n-methyl-n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C)C=C1 CXLBYPJSAWOYSI-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Metal Rolling (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0080987 | 1965-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1259872B true DE1259872B (de) | 1968-02-01 |
Family
ID=6980920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1259872D Pending DE1259872B (de) | 1965-03-16 | Verfahren zur Herstellung von Sulfonylurethanen bzw. deren Salzen |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT260944B (enrdf_load_stackoverflow) |
| BR (1) | BR6677873D0 (enrdf_load_stackoverflow) |
| CH (1) | CH459184A (enrdf_load_stackoverflow) |
| DE (1) | DE1259872B (enrdf_load_stackoverflow) |
| DK (1) | DK113360B (enrdf_load_stackoverflow) |
| FI (1) | FI44596C (enrdf_load_stackoverflow) |
| FR (1) | FR1471089A (enrdf_load_stackoverflow) |
| LU (1) | LU50655A1 (enrdf_load_stackoverflow) |
| NL (2) | NL6603399A (enrdf_load_stackoverflow) |
| NO (1) | NO119532B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993010086A1 (de) * | 1991-11-13 | 1993-05-27 | MTA Központi Kémiai Kutató Intézete | Verfahren zur herstellung von n-(arylsulfonyl)-carbamid-säure-derivaten und den in diesem verfahren verwendbaren intermedieren |
| FR2690918B1 (fr) * | 1992-05-06 | 2001-12-28 | Poudres & Explosifs Ste Nale | Utilisation d'un arylsulfonyluréthanne comme résine garnissante dans les vernis à ongles nitrocellulosiques. Nouveaux arylsulfonyluréthannes et nouveaux vernis à ongles nitrocellulosiques. |
| DK0612724T3 (da) * | 1993-02-23 | 1997-06-16 | Hoechst Ag | Substituerede benzensulfonylurinstoffer og -thiourinstoffer, fremgangsmåde til deres fremstilling og deres anvendelse som farmaceutika |
-
0
- NL NL128362D patent/NL128362C/xx active
- DE DENDAT1259872D patent/DE1259872B/de active Pending
-
1966
- 1966-03-10 DK DK125366A patent/DK113360B/da unknown
- 1966-03-14 FR FR53305A patent/FR1471089A/fr not_active Expired
- 1966-03-14 AT AT242866A patent/AT260944B/de active
- 1966-03-14 CH CH360666A patent/CH459184A/de unknown
- 1966-03-15 NO NO16211066A patent/NO119532B/no unknown
- 1966-03-15 FI FI65366A patent/FI44596C/fi active
- 1966-03-15 LU LU50655D patent/LU50655A1/xx unknown
- 1966-03-15 BR BR17787366A patent/BR6677873D0/pt unknown
- 1966-03-16 NL NL6603399A patent/NL6603399A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK113360B (da) | 1969-03-17 |
| FR1471089A (fr) | 1967-02-24 |
| FI44596C (fi) | 1971-12-10 |
| AT260944B (de) | 1968-03-25 |
| LU50655A1 (enrdf_load_stackoverflow) | 1966-05-16 |
| CH459184A (de) | 1968-07-15 |
| FI44596B (enrdf_load_stackoverflow) | 1971-08-31 |
| NO119532B (enrdf_load_stackoverflow) | 1970-06-01 |
| NL128362C (enrdf_load_stackoverflow) | |
| BR6677873D0 (pt) | 1973-09-11 |
| NL6603399A (enrdf_load_stackoverflow) | 1966-09-19 |
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