GB690238A - Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine - Google Patents
Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidineInfo
- Publication number
- GB690238A GB690238A GB19568/50A GB1956850A GB690238A GB 690238 A GB690238 A GB 690238A GB 19568/50 A GB19568/50 A GB 19568/50A GB 1956850 A GB1956850 A GB 1956850A GB 690238 A GB690238 A GB 690238A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- methylaminopropane
- chloro
- heating
- hydrochloride
- 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
- GMFUTRCIEWHKBH-UHFFFAOYSA-N 3,4-dimethyl-5-phenyl-1,3-thiazolidin-2-imine Chemical compound S1C(=N)N(C)C(C)C1C1=CC=CC=C1 GMFUTRCIEWHKBH-UHFFFAOYSA-N 0.000 title abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 6
- 238000010438 heat treatment Methods 0.000 abstract 6
- ICZRAESMLGJTOQ-UHFFFAOYSA-N 1-chloro-n-methyl-1-phenylpropan-2-amine;hydrochloride Chemical compound Cl.CNC(C)C(Cl)C1=CC=CC=C1 ICZRAESMLGJTOQ-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 5
- 239000000725 suspension Substances 0.000 abstract 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- MHGMILWHOHIJBP-UHFFFAOYSA-N [2-(methylamino)-1-phenylpropyl] thiocyanate Chemical compound CNC(C)C(SC#N)C1=CC=CC=C1 MHGMILWHOHIJBP-UHFFFAOYSA-N 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- GMFUTRCIEWHKBH-HNHGDDPOSA-N (4R)-3,4-dimethyl-5-phenyl-1,3-thiazolidin-2-imine Chemical compound CN1C(SC([C@H]1C)C1=CC=CC=C1)=N GMFUTRCIEWHKBH-HNHGDDPOSA-N 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 abstract 1
- 229960002179 ephedrine Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 3,4-dimethyl-5-phenyl-2-iminothiazolidine in its racemic and in its optically active forms, and also its preparation by the action of a salt of thiocyanic acid on 1 - phenyl - 1 - halogen - 2 - methylaminopropane hydrohalide in the presence of a solvent or suspension medium and preferably in an alkaline medium. In a modification, the reaction components are first heated in an acid medium and the 1-phenyl-1-thiocyan-2-methylaminopropane so formed is then heated in an alkaline medium. The optically active products are obtained by starting from the optically active 1-phenyl-1-halogen - 2 - methylaminopropane hydrohalogenides. Suitable solvents or suspension media are water, methanol, ethanol, butyl ether, chlorinated hydrocarbons, benzene and pyridine, and suitable alkaline materials are caustic alkali, ammonia, methylamine, aniline, ephedrine, pyridine and quinoline. In example (1), racemic 1 - phenyl - 1 - chloro - 2 - methylaminopropane hydrochloride is suspended in ethyl alcohol with ammonium thiocyanate and caustic soda or caustic potash and heated under reflux to yield the thiocyanate of 3,4-dimethyl - 5 - phenyl - 2 - iminothiazolidine; l - 1 - phenyl - 1 - chloro - 2 - methylaminopropane hydrochloride similarly treated yields the salt of d-3,4-dimethyl-5-phenyl-2-iminothiazolidine, and vice versa. In other examples, the thiocyanic salt of 3,4-dimethyl-5-phenyl-2-iminothiazolidine is prepared by (2) heating a suspension of 1-phenyl-1-chloro-2-methylaminopropane hydrochloride in an aqueous solution of ammonium thiocyanate and sodium acetate; (3) heating a suspension of 1-phenyl-1-chloro-2-methylaminopropane hydrochloride with ammonium thiocyanate and a little hydrochloric acid, and heating the 1-phenyl-1-thiocyan-2-methylaminopropane hydrothiocyanate so formed in aqueous caustic soda; (4) heating 1-phenyl-1-chloro - 2 - methylaminopropane hydrochloride and ammonium thiocyanate in a mixture of ethylene chloride and pyridine; (5) heating a mixture of 1-phenyl-1-chloro-2-methylaminopropane hydrochloride, ammonium thiocyanate and l - 1 - phenyl - 1 - oxy - 2 - methylaminopropane suspended in ethylene chloride; and (6) by heating the thiocyanic acid salt of 1-phenyl-1-thiocyano-2-methylaminopropane and caustic soda in water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US690238XA | 1949-08-23 | 1949-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB690238A true GB690238A (en) | 1953-04-15 |
Family
ID=22086217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19568/50A Expired GB690238A (en) | 1949-08-23 | 1950-08-04 | Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB690238A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1001281B (en) * | 1953-10-29 | 1957-01-24 | Cassella Farbwerke Mainkur Ag | Process for the production of therapeutically valuable rhodane compounds |
| FR2024952A1 (en) * | 1968-11-29 | 1970-09-04 | Sandoz Sa | |
| FR2034463A1 (en) * | 1969-01-13 | 1970-12-11 | Sandoz Sa | |
| US4665083A (en) * | 1984-04-25 | 1987-05-12 | Egis Gyogyszergyar | Iminothiazolidine derivatives |
-
1950
- 1950-08-04 GB GB19568/50A patent/GB690238A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1001281B (en) * | 1953-10-29 | 1957-01-24 | Cassella Farbwerke Mainkur Ag | Process for the production of therapeutically valuable rhodane compounds |
| FR2024952A1 (en) * | 1968-11-29 | 1970-09-04 | Sandoz Sa | |
| FR2034463A1 (en) * | 1969-01-13 | 1970-12-11 | Sandoz Sa | |
| US4665083A (en) * | 1984-04-25 | 1987-05-12 | Egis Gyogyszergyar | Iminothiazolidine derivatives |
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