DE2617918C3 - Verfahren zur Herstellung von Carbamidsäureestern und Thiocarbamidsäure-S-estern - Google Patents
Verfahren zur Herstellung von Carbamidsäureestern und Thiocarbamidsäure-S-esternInfo
- Publication number
- DE2617918C3 DE2617918C3 DE2617918A DE2617918A DE2617918C3 DE 2617918 C3 DE2617918 C3 DE 2617918C3 DE 2617918 A DE2617918 A DE 2617918A DE 2617918 A DE2617918 A DE 2617918A DE 2617918 C3 DE2617918 C3 DE 2617918C3
- Authority
- DE
- Germany
- Prior art keywords
- esters
- acid
- preparation
- mmol
- thiocarbamic
- 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 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 5
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- LADHHNUVWRWPRH-UHFFFAOYSA-N s-methyl carbamothioate Chemical compound CSC(N)=O LADHHNUVWRWPRH-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012973 diazabicyclooctane Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- NUZMVZBBZQPQSS-UHFFFAOYSA-O C[S+]=C(N)O Chemical class C[S+]=C(N)O NUZMVZBBZQPQSS-UHFFFAOYSA-O 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical compound C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/26—Polythioesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22616/75A IT1037577B (it) | 1975-04-23 | 1975-04-23 | Procedimento per la transesterificazione di esteri di acidi tiocarbammici |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2617918A1 DE2617918A1 (de) | 1976-10-28 |
| DE2617918B2 DE2617918B2 (de) | 1981-02-12 |
| DE2617918C3 true DE2617918C3 (de) | 1981-12-24 |
Family
ID=11198467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2617918A Expired DE2617918C3 (de) | 1975-04-23 | 1976-04-23 | Verfahren zur Herstellung von Carbamidsäureestern und Thiocarbamidsäure-S-estern |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS51128918A (enExample) |
| AT (1) | ATA294276A (enExample) |
| AU (1) | AU501786B2 (enExample) |
| BE (1) | BE841007A (enExample) |
| CA (1) | CA1076131A (enExample) |
| DE (1) | DE2617918C3 (enExample) |
| DK (1) | DK180076A (enExample) |
| ES (1) | ES447392A1 (enExample) |
| FR (1) | FR2308614A1 (enExample) |
| GB (1) | GB1507429A (enExample) |
| IE (1) | IE42800B1 (enExample) |
| IL (1) | IL49429A0 (enExample) |
| IN (1) | IN144588B (enExample) |
| IT (1) | IT1037577B (enExample) |
| LU (1) | LU74809A1 (enExample) |
| NL (1) | NL7604302A (enExample) |
| NO (1) | NO761374L (enExample) |
| PT (1) | PT65033B (enExample) |
| RO (1) | RO69169A (enExample) |
| SE (1) | SE431449B (enExample) |
| YU (1) | YU100776A (enExample) |
| ZA (1) | ZA762148B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH649078A5 (de) * | 1980-01-25 | 1985-04-30 | Reanal Finomvegyszergyar | Verfahren zur herstellung von n-mono- oder disubstituierten n-aryl-harnstoff-derivaten. |
| US5621132A (en) * | 1992-10-19 | 1997-04-15 | Council Of Scientific And Industrial Research | Process for making alkyl N-alkyl or N-aryl-thiocarbamates |
-
1975
- 1975-04-23 IT IT22616/75A patent/IT1037577B/it active
-
1976
- 1976-04-09 ZA ZA762148A patent/ZA762148B/xx unknown
- 1976-04-15 GB GB15729/76A patent/GB1507429A/en not_active Expired
- 1976-04-16 IL IL49429A patent/IL49429A0/xx unknown
- 1976-04-20 CA CA250,553A patent/CA1076131A/en not_active Expired
- 1976-04-20 YU YU01007/76A patent/YU100776A/xx unknown
- 1976-04-20 AU AU13114/76A patent/AU501786B2/en not_active Expired
- 1976-04-21 LU LU74809A patent/LU74809A1/xx unknown
- 1976-04-21 DK DK180076A patent/DK180076A/da not_active Application Discontinuation
- 1976-04-21 ES ES447392A patent/ES447392A1/es not_active Expired
- 1976-04-22 NL NL7604302A patent/NL7604302A/xx not_active Application Discontinuation
- 1976-04-22 AT AT762942A patent/ATA294276A/de not_active IP Right Cessation
- 1976-04-22 FR FR7611954A patent/FR2308614A1/fr active Granted
- 1976-04-22 SE SE7604668A patent/SE431449B/xx unknown
- 1976-04-22 PT PT65033A patent/PT65033B/pt unknown
- 1976-04-22 NO NO761374A patent/NO761374L/no unknown
- 1976-04-22 RO RO7685763A patent/RO69169A/ro unknown
- 1976-04-22 BE BE166371A patent/BE841007A/xx not_active IP Right Cessation
- 1976-04-23 DE DE2617918A patent/DE2617918C3/de not_active Expired
- 1976-04-23 JP JP51045612A patent/JPS51128918A/ja active Pending
- 1976-04-23 IN IN704/CAL/76A patent/IN144588B/en unknown
- 1976-04-23 IE IE866/76A patent/IE42800B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1076131A (en) | 1980-04-22 |
| AU501786B2 (en) | 1979-06-28 |
| DE2617918A1 (de) | 1976-10-28 |
| SE7604668L (sv) | 1976-10-24 |
| JPS51128918A (en) | 1976-11-10 |
| FR2308614A1 (fr) | 1976-11-19 |
| IT1037577B (it) | 1979-11-20 |
| NO761374L (enExample) | 1976-10-26 |
| FR2308614B1 (enExample) | 1980-04-11 |
| IE42800L (en) | 1976-10-23 |
| DE2617918B2 (de) | 1981-02-12 |
| ATA294276A (de) | 1978-06-15 |
| PT65033A (en) | 1976-05-01 |
| SE431449B (sv) | 1984-02-06 |
| ES447392A1 (es) | 1977-07-01 |
| BE841007A (fr) | 1976-10-22 |
| PT65033B (en) | 1977-09-12 |
| IL49429A0 (en) | 1976-06-30 |
| ZA762148B (en) | 1977-04-27 |
| NL7604302A (nl) | 1976-10-26 |
| IE42800B1 (en) | 1980-10-22 |
| YU100776A (en) | 1982-10-31 |
| IN144588B (enExample) | 1978-05-20 |
| LU74809A1 (enExample) | 1977-01-12 |
| GB1507429A (en) | 1978-04-12 |
| DK180076A (da) | 1976-10-24 |
| AU1311476A (en) | 1977-10-27 |
| RO69169A (ro) | 1981-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |