JPS6016413B2 - ４―アルキル―チオセミカルバジド類の製造方法 - Google Patents
４―アルキル―チオセミカルバジド類の製造方法Info
- Publication number
- JPS6016413B2 JPS6016413B2 JP51121966A JP12196676A JPS6016413B2 JP S6016413 B2 JPS6016413 B2 JP S6016413B2 JP 51121966 A JP51121966 A JP 51121966A JP 12196676 A JP12196676 A JP 12196676A JP S6016413 B2 JPS6016413 B2 JP S6016413B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mol
- alkyl
- heating
- carried out
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 33
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012990 dithiocarbamate Substances 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 description 3
- -1 alkyl mercaptans Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UMEJBYJALNGUQF-UHFFFAOYSA-N 5-tert-butyl-n-methyl-1,3,4-thiadiazol-2-amine Chemical compound CNC1=NN=C(C(C)(C)C)S1 UMEJBYJALNGUQF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 229910017849 NH2—NH2 Inorganic materials 0.000 description 1
- 238000007290 Pedersen coupling reaction Methods 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2546096.2 | 1975-10-15 | ||
| DE2546096A DE2546096C2 (de) | 1975-10-15 | 1975-10-15 | Verfahren zur Herstellung von 4-Alkyl- thiosemicarbaziden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5251321A JPS5251321A (en) | 1977-04-25 |
| JPS6016413B2 true JPS6016413B2 (ja) | 1985-04-25 |
Family
ID=5959158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51121966A Expired JPS6016413B2 (ja) | 1975-10-15 | 1976-10-13 | ４―アルキル―チオセミカルバジド類の製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4132736A (en, 2012) |
| JP (1) | JPS6016413B2 (en, 2012) |
| AT (1) | AT349032B (en, 2012) |
| BE (1) | BE847331A (en, 2012) |
| BR (1) | BR7606874A (en, 2012) |
| CH (1) | CH620427A5 (en, 2012) |
| DE (1) | DE2546096C2 (en, 2012) |
| DK (1) | DK463976A (en, 2012) |
| FR (1) | FR2327987A1 (en, 2012) |
| GB (1) | GB1506790A (en, 2012) |
| IL (1) | IL50667A (en, 2012) |
| IT (1) | IT1068949B (en, 2012) |
| NL (1) | NL7611271A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172092A (en) * | 1975-12-17 | 1979-10-23 | Mobay Chemical Corporation | Production of thiocarbohydrazide |
| DE2658557A1 (de) * | 1976-12-23 | 1978-06-29 | Bayer Ag | Verfahren zur herstellung von thiocarbohydrazid in technischem massstab |
| DE2723121C2 (de) * | 1977-05-23 | 1979-04-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Alkylthiosemicarbaziden |
| US4237066A (en) * | 1978-10-26 | 1980-12-02 | Mobay Chemical Corporation | Preparation of lower alkyl thiosemicarbazides |
| US4853483A (en) * | 1986-11-06 | 1989-08-01 | Ici Americas Inc. | Preparation of alkyl thiosemicarbazides |
| DE68919894T2 (de) * | 1988-04-27 | 1995-05-04 | Dowelanco | Synthese von 4-Methyl-3-thiosemicarbazid. |
| EP2305218A1 (en) * | 1999-10-29 | 2011-04-06 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
| CN105884668B (zh) * | 2016-04-22 | 2018-01-16 | 山东汇海医药化工有限公司 | 一种基于石墨烯提高2‑甲基氨基硫脲收率的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD83559A (en, 2012) * | ||||
| CA634690A (en) * | 1962-01-16 | Applegath Fred | Diureides and process for the preparation thereof | |
| US2657234A (en) * | 1949-12-12 | 1953-10-27 | Schenley Ind Inc | Preparation of thiosemicarbazides |
| US3539587A (en) * | 1964-03-27 | 1970-11-10 | Standard Oil Co | Method of preparing cyclic ureas from n,n-dialkylammonium n,n-dialkyl monothiol carbamates and diprimaryamines |
| DE1767924A1 (de) | 1968-07-02 | 1971-10-07 | Bayer Ag | 1-Phenyl-4,4-dialkyl-thiosemicarbazide |
| GB1431654A (en) * | 1972-04-05 | 1976-04-14 | Quimco Gmbh | Process for the preparation of trisubstituted ureas |
| US3929877A (en) * | 1973-11-26 | 1975-12-30 | Akzo N V Of Arnhem Holland | Process for the production of thiocarbohydrazide |
-
1975
- 1975-10-15 DE DE2546096A patent/DE2546096C2/de not_active Expired
-
1976
- 1976-10-06 US US05/729,933 patent/US4132736A/en not_active Expired - Lifetime
- 1976-10-11 GB GB42131/76A patent/GB1506790A/en not_active Expired
- 1976-10-12 CH CH1288176A patent/CH620427A5/de not_active IP Right Cessation
- 1976-10-12 IL IL50667A patent/IL50667A/xx unknown
- 1976-10-12 NL NL7611271A patent/NL7611271A/xx not_active Application Discontinuation
- 1976-10-13 JP JP51121966A patent/JPS6016413B2/ja not_active Expired
- 1976-10-13 IT IT28281/76A patent/IT1068949B/it active
- 1976-10-14 DK DK463976A patent/DK463976A/da unknown
- 1976-10-14 BR BR7606874A patent/BR7606874A/pt unknown
- 1976-10-15 FR FR7631176A patent/FR2327987A1/fr active Granted
- 1976-10-15 BE BE171541A patent/BE847331A/xx not_active IP Right Cessation
- 1976-10-15 AT AT768476A patent/AT349032B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2546096C2 (de) | 1983-08-25 |
| BR7606874A (pt) | 1977-08-30 |
| IL50667A (en) | 1979-12-30 |
| JPS5251321A (en) | 1977-04-25 |
| US4132736A (en) | 1979-01-02 |
| DE2546096A1 (de) | 1977-04-21 |
| FR2327987A1 (fr) | 1977-05-13 |
| BE847331A (fr) | 1977-04-15 |
| IT1068949B (it) | 1985-03-21 |
| AT349032B (de) | 1979-03-12 |
| GB1506790A (en) | 1978-04-12 |
| DK463976A (da) | 1977-04-16 |
| FR2327987B1 (en, 2012) | 1981-06-19 |
| CH620427A5 (en, 2012) | 1980-11-28 |
| IL50667A0 (en) | 1976-12-31 |
| ATA768476A (de) | 1978-08-15 |
| NL7611271A (nl) | 1977-04-19 |
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