CH416601A - Procédé de préparation de nouveaux diisothiocyanates - Google Patents
Procédé de préparation de nouveaux diisothiocyanatesInfo
- Publication number
- CH416601A CH416601A CH814863A CH814863A CH416601A CH 416601 A CH416601 A CH 416601A CH 814863 A CH814863 A CH 814863A CH 814863 A CH814863 A CH 814863A CH 416601 A CH416601 A CH 416601A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclohexane
- diisothiocyanates
- thiophosgene
- bis
- starting
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 9
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- -1 2-isothiocyanato-ethyl Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RWLDYZLAMWRCJQ-UHFFFAOYSA-N 1,4-diisothiocyanatocyclohexane Chemical compound S=C=NC1CCC(N=C=S)CC1 RWLDYZLAMWRCJQ-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- TTZOIUBKLIHRCU-UHFFFAOYSA-N 1,3-diisothiocyanatocyclohexane Chemical compound S=C=NC1CCCC(N=C=S)C1 TTZOIUBKLIHRCU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 210000004081 cilia Anatomy 0.000 description 1
- QFSPGQSXKARDIH-UHFFFAOYSA-N cyclohexane;dihydrochloride Chemical compound Cl.Cl.C1CCCCC1 QFSPGQSXKARDIH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/30—Isothiocyanates containing at least two isothiocyanate groups bound to the same carbon skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH579866A CH468983A (fr) | 1962-07-06 | 1963-07-01 | Procédé de préparation de nouveaux diisothiocyanates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR903216A FR1403621A (fr) | 1962-07-06 | 1962-07-06 | Nouveaux diisothiocyanates et leur préparation |
| FR922064A FR85305E (fr) | 1963-01-21 | 1963-01-21 | Nouveaux diisothiocyanates et leur préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH416601A true CH416601A (fr) | 1966-07-15 |
Family
ID=26196530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH814863A CH416601A (fr) | 1962-07-06 | 1963-07-01 | Procédé de préparation de nouveaux diisothiocyanates |
Country Status (8)
| Country | Link |
|---|---|
| AT (2) | AT244930B (en, 2012) |
| CH (1) | CH416601A (en, 2012) |
| DK (2) | DK107805C (en, 2012) |
| ES (1) | ES289623A1 (en, 2012) |
| GB (1) | GB999221A (en, 2012) |
| LU (1) | LU43855A1 (en, 2012) |
| NL (1) | NL136602C (en, 2012) |
| SE (1) | SE315277B (en, 2012) |
-
0
- NL NL136602D patent/NL136602C/xx active
-
1963
- 1963-06-05 LU LU43855D patent/LU43855A1/xx unknown
- 1963-07-01 CH CH814863A patent/CH416601A/fr unknown
- 1963-07-03 DK DK315863A patent/DK107805C/da active
- 1963-07-03 DK DK547364A patent/DK106794C/da active
- 1963-07-04 ES ES289623A patent/ES289623A1/es not_active Expired
- 1963-07-04 GB GB2663263A patent/GB999221A/en not_active Expired
- 1963-07-04 SE SE743063A patent/SE315277B/xx unknown
- 1963-07-08 AT AT211165A patent/AT244930B/de active
- 1963-07-08 AT AT544563A patent/AT244927B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| NL136602C (en, 2012) | |
| SE315277B (en, 2012) | 1969-09-29 |
| DK107805C (da) | 1967-07-10 |
| AT244927B (de) | 1966-02-10 |
| DK106794C (da) | 1967-03-20 |
| GB999221A (en) | 1965-07-21 |
| AT244930B (de) | 1966-02-10 |
| LU43855A1 (en, 2012) | 1963-08-05 |
| ES289623A1 (es) | 1963-11-01 |
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