CH555815A - Verfahren zur herstellung von sulfonylharnstoffen. - Google Patents
Verfahren zur herstellung von sulfonylharnstoffen.Info
- Publication number
- CH555815A CH555815A CH265571A CH265571A CH555815A CH 555815 A CH555815 A CH 555815A CH 265571 A CH265571 A CH 265571A CH 265571 A CH265571 A CH 265571A CH 555815 A CH555815 A CH 555815A
- Authority
- CH
- Switzerland
- Prior art keywords
- endo
- hydroxy
- urea
- tolylsulfonylurea
- acetonitrile
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000004202 carbamide Substances 0.000 claims abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003672 ureas Chemical class 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- FHTLRVQASCAGSZ-UHFFFAOYSA-N (2-methylphenyl)sulfonylurea Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(N)=O FHTLRVQASCAGSZ-UHFFFAOYSA-N 0.000 claims description 2
- TYMBLCCPQXGEHE-UHFFFAOYSA-N (3-methylphenyl)sulfonylurea Chemical compound CC1=CC=CC(S(=O)(=O)NC(N)=O)=C1 TYMBLCCPQXGEHE-UHFFFAOYSA-N 0.000 claims description 2
- WNKXODCQOYNQBC-UHFFFAOYSA-N (4-ethylphenyl)sulfonylurea Chemical compound CCC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 WNKXODCQOYNQBC-UHFFFAOYSA-N 0.000 claims description 2
- NZDKIPXYRSHTBE-UHFFFAOYSA-N C(CC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)N Chemical compound C(CC)C1=CC=C(C=C1)S(=O)(=O)NC(=O)N NZDKIPXYRSHTBE-UHFFFAOYSA-N 0.000 claims description 2
- 229940127003 anti-diabetic drug Drugs 0.000 claims description 2
- 239000003472 antidiabetic agent Substances 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229940116229 borneol Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 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
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2118170A | 1970-03-19 | 1970-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH555815A true CH555815A (de) | 1974-11-15 |
Family
ID=21802797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH265571A CH555815A (de) | 1970-03-19 | 1971-02-24 | Verfahren zur herstellung von sulfonylharnstoffen. |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS4935617B1 (en, 2012) |
| AT (1) | AT304563B (en, 2012) |
| CH (1) | CH555815A (en, 2012) |
| CS (1) | CS157100B2 (en, 2012) |
| DK (1) | DK135581B (en, 2012) |
| ES (1) | ES389358A1 (en, 2012) |
| FI (1) | FI54101C (en, 2012) |
| NL (1) | NL164554C (en, 2012) |
| NO (1) | NO130232B (en, 2012) |
| PL (1) | PL85167B1 (en, 2012) |
| RO (1) | RO61398A (en, 2012) |
| SE (1) | SE373126B (en, 2012) |
| YU (1) | YU33720B (en, 2012) |
-
1971
- 1971-02-24 CH CH265571A patent/CH555815A/de not_active IP Right Cessation
- 1971-03-01 NL NL7102688A patent/NL164554C/xx not_active IP Right Cessation
- 1971-03-01 FI FI60071A patent/FI54101C/fi active
- 1971-03-01 NO NO76471A patent/NO130232B/no unknown
- 1971-03-12 DK DK119571A patent/DK135581B/da unknown
- 1971-03-15 SE SE333071A patent/SE373126B/xx unknown
- 1971-03-16 YU YU65771A patent/YU33720B/xx unknown
- 1971-03-18 RO RO6631071A patent/RO61398A/ro unknown
- 1971-03-18 ES ES389358A patent/ES389358A1/es not_active Expired
- 1971-03-18 AT AT233471A patent/AT304563B/de not_active IP Right Cessation
- 1971-03-18 CS CS198571A patent/CS157100B2/cs unknown
- 1971-03-19 JP JP46015715A patent/JPS4935617B1/ja active Pending
- 1971-03-19 PL PL14702171A patent/PL85167B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT304563B (de) | 1973-01-10 |
| CS157100B2 (en, 2012) | 1974-08-23 |
| NL164554B (nl) | 1980-08-15 |
| NO130232B (en, 2012) | 1974-07-29 |
| NL7102688A (en, 2012) | 1971-09-21 |
| FI54101C (fi) | 1978-10-10 |
| YU33720B (en) | 1978-02-28 |
| PL85167B1 (en, 2012) | 1976-04-30 |
| DK135581C (en, 2012) | 1977-10-31 |
| NL164554C (nl) | 1981-01-15 |
| YU65771A (en) | 1977-08-31 |
| DK135581B (da) | 1977-05-23 |
| ES389358A1 (es) | 1973-06-01 |
| SE373126B (en, 2012) | 1975-01-27 |
| FI54101B (fi) | 1978-06-30 |
| JPS4935617B1 (en, 2012) | 1974-09-25 |
| RO61398A (en, 2012) | 1976-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |