CH338465A - Process for the preparation of dimethyl-dithio-hydantoin - Google Patents
Process for the preparation of dimethyl-dithio-hydantoinInfo
- Publication number
- CH338465A CH338465A CH338465DA CH338465A CH 338465 A CH338465 A CH 338465A CH 338465D A CH338465D A CH 338465DA CH 338465 A CH338465 A CH 338465A
- Authority
- CH
- Switzerland
- Prior art keywords
- alcohol
- acetone
- dimethyl
- dithio
- hydantoin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- NLEGOBBGDOATPO-UHFFFAOYSA-N 5,5-dimethylimidazolidine-2,4-dithione Chemical compound CC1(C)NC(=S)NC1=S NLEGOBBGDOATPO-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Procédé pour la préparation de diméthyl-dithio-hydantoïne L'invention a pour objet un procédé de fabrica tion de 5,5-diméthyl-2,4-dithio-hydantoïne corres pondant à la formule suivante
EMI0001.0005
Le procédé peut être mis en aeuvre de la ma nière suivante Un matras de 5 à 10 litres pourvu d'un grand réfrigérant à reflux est chargé de 445 g de cyanure de sodium ou de potassium, 481 g de chlorure d'am monium, 507 g d'acétone, 665 g de sulfure de car bone et 2, 1 1 d'alcool à 850.
On chauffe ce mélange doucement jusqu'à ébullition et continue le reflux pendant 24 à 30 heures, sur quoi on distille le sol vant (alcool) et on élimine par entraînement à la vapeur les derniers restes d'acétone ou de sulfure de carbure ayant pu rester sans réagir.
Le produit solide obtenu est dissous dans la soude à 10 % en chauffant au bain-marie. La solu- tion alcaline est ensuite précipitée avec de l'acide chlorhydrique concentré jusqu'à réaction acide du papier bleu de tournesol et filtrée. Le produit ob tenu est cristallisé dans l'eau où il forme des aiguilles brillantes de couleur jaune clair et d'un
point de fusion de 1430.
Le produit donne à l'analyse les pourcentages suivants C = 35,44 0/0 H = 5,00 % N = 16,95 0/0 S = 40,16'% les valeurs calculées pour la 5,5-diméthyl-dithio- hydantoïne étant de C = 37,45 1% H = 5 /o N = 17,50 0/0 S = 40,
00 0/0 Ce produit est stable jusqu'à la température de 2700 environ et commence à se décomposer à cette température avec dégagement d'acide sulfhydrique et formation d'un goudron noir.
On peut le recristalliser sans changement dans l'acide chlorhydrique 6n. Il forme un sel de mercure stable à la température d'ébullition de l'eau.
La diméthyl-dithio-hydantoïne réagit à froid avec le peroxyde d'hydrogène ammoniacal en formant la 5,5-diméthyl-hydantdine. La réaction avec de l'oxyde d'argent et de l'acide chlorhydrique concentré bouil lant donne un composé correspondant, selon l'ana lyse, à la 5,5-diméthyl-4-thiohydantdine.
Le produit obtenu par ce procédé est efficace contre des maladies endocriniennes et du système nerveux.
Process for the preparation of dimethyl-dithio-hydantoin The object of the invention is a process for the manufacture of 5,5-dimethyl-2,4-dithio-hydantoin corresponding to the following formula
EMI0001.0005
The process can be carried out in the following way A 5 to 10 liter flask fitted with a large reflux condenser is charged with 445 g of sodium or potassium cyanide, 481 g of ammonium chloride, 507 g of acetone, 665 g of carbon disulphide and 2.11 of 850 alcohol.
This mixture is gently heated to boiling and refluxed for 24 to 30 hours, whereupon the boiling sol (alcohol) is distilled off and any last remaining acetone or carbide sulfide which may have been removed by steam stripping. remain without reacting.
The solid product obtained is dissolved in 10% sodium hydroxide while heating in a water bath. The alkaline solution is then precipitated with concentrated hydrochloric acid until the litmus blue paper reacts acidic and filtered. The product obtained is crystallized in water where it forms shiny needles of light yellow color and of a
melting point of 1430.
The product gives the following percentages on analysis C = 35.44 0/0 H = 5.00% N = 16.95 0/0 S = 40.16% the values calculated for 5,5-dimethyl- dithio-hydantoin being C = 37.45 1% H = 5 / o N = 17.50 0/0 S = 40,
00 0/0 This product is stable up to a temperature of about 2700 and begins to decompose at this temperature with evolution of hydrogen sulphide and formation of a black tar.
It can be recrystallized without change from 6n hydrochloric acid. It forms a stable mercury salt at the boiling temperature of water.
Dimethyl-dithio-hydantoin reacts in the cold with ammoniacal hydrogen peroxide to form 5,5-dimethyl-hydantdine. The reaction with silver oxide and boiling concentrated hydrochloric acid gives a compound corresponding, according to analysis, to 5,5-dimethyl-4-thiohydantdine.
The product obtained by this process is effective against endocrine and nervous system diseases.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES338465X | 1955-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH338465A true CH338465A (en) | 1959-05-31 |
Family
ID=8245128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH338465D CH338465A (en) | 1955-03-15 | 1956-03-07 | Process for the preparation of dimethyl-dithio-hydantoin |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH338465A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189587A (en) * | 1977-04-05 | 1980-02-19 | Ciba-Geigy Corporation | 1,3-Diaminomethyl-hydantoin additives for lubricating oils |
-
1956
- 1956-03-07 CH CH338465D patent/CH338465A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189587A (en) * | 1977-04-05 | 1980-02-19 | Ciba-Geigy Corporation | 1,3-Diaminomethyl-hydantoin additives for lubricating oils |
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