GB817745A - 2-thiohydantoins - Google Patents
2-thiohydantoinsInfo
- Publication number
- GB817745A GB817745A GB3819856A GB3819856A GB817745A GB 817745 A GB817745 A GB 817745A GB 3819856 A GB3819856 A GB 3819856A GB 3819856 A GB3819856 A GB 3819856A GB 817745 A GB817745 A GB 817745A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- methyl
- dimethyl
- acid
- prepared
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- 230000000875 corresponding Effects 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- -1 polymethylene ring Polymers 0.000 abstract 3
- NCTOGJVAFQWQOR-UHFFFAOYSA-N 2-anilino-2-methylpropanenitrile Chemical compound N#CC(C)(C)NC1=CC=CC=C1 NCTOGJVAFQWQOR-UHFFFAOYSA-N 0.000 abstract 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N Hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- CIAAEGBIIUWFGL-UHFFFAOYSA-N 2-anilino-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)NC1=CC=CC=C1 CIAAEGBIIUWFGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N 420-05-3 Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 Acetic Acid Drugs 0.000 abstract 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N Ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N Thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- UWGOFVUXIYSLPD-UHFFFAOYSA-N [C-]#N.[Na+].NC1=CC=CC=C1 Chemical compound [C-]#N.[Na+].NC1=CC=CC=C1 UWGOFVUXIYSLPD-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
- 150000003862 amino acid derivatives Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 101700061999 nhr-3 Proteins 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 2-thiohydantoins of the formula <FORM:0817745/IV (b)/1> wherein R1 and R2 are each alkyl groups or together form with the adjacent carbon atom a polymethylene ring, and R3 is a phenyl group which may be substituted by alkyl groups or halogen atoms, and the manufacture thereof by partial desulphurization of the corresponding dithiohydantoins:- <FORM:0817745/IV (b)/2> by interaction either with ammonia or with a primary amino-compound, in an aqueous medium followed by hydrolysis of the product so formed in an acid medium. The invention also comprises the manufacture of 5 : 5-dimethyl - 1 - phenyl - 2 - thiohydantoin by heating alpha-anilino isobutyronitrile with thiocyanic acid or a salt thereof, such as the sodium, potassium or ammonium salt, in the presence of acetic anhydride. In an example, 5 : 5-dimethyl - 1 - phenyl - 2 : 4 - dithiohydantoin is reacted with 2-aminoethanol in water to form 4 - (beta - hydroxyethylimino) - 5 : 5 - dimethyl - 1-phenyl-2-thiohydantoin which is then hydrolysed by hydrochloric acid to give 5 : 5-dimethyl - 1 - phenyl - 2 - thiohydantoin. Similarly are prepared compounds of formula (I) wherein R1 and R2 are each ethyl, methyl and ethyl, or methyl and isobutyl, or together pentamethylene, and R3 is phenyl, and wherein R1 and R2 are each methyl and R3 is p-tolyl or m- or p-chlorophenyl, the corresponding 4-(betahydroxyethylimino)-compounds being isolated. (In the hydrolysis step to form the 2-thiohydantoins where R3 is phenyl and R1 and R2 are methyl and ethyl, and methyl and isobutyl, the hydrochloride salts of the ethylimino compounds are also isolated.) Another example describes the preparation of the 5 : 5-dimethyl-1-phenyl-2-thiohydantoin by reacting alphaanilino-isobutyronitrile with ammonium thiocyanate in acetic anhydride. Dithiohydantoins of formula (II) are prepared by reacting the corresponding hydantoins: <FORM:0817745/IV (b)/3> with phosphorus pentasulphide, in an inert solvent, such as tetrahydronaphthalene, whilst hydantoins of formula (III) are prepared by reacting a substituted aminoacid derivative of the formula R1R2C(NHR3)X, wherein X is a carboxy group or a functional derivative or precursor thereof, particularly a cyano group, with cyanic acid, followed, if necessary, as, for example when X is a cyano group, by hydrolysis with an acid such as hydrochloric acid. Alpha-anilino-alpha-isobutyl-propionitrile is prepared from isobutyl methyl ketone, aniline sodium cyanide and glacial acetic acid, whilst similarly are prepared alpha-p- and m-chloranilino-isobutyronitriles.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB817745A true GB817745A (en) | 1959-08-06 |
Family
ID=1745191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3819856A Expired GB817745A (en) | 1956-12-14 | 2-thiohydantoins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB817745A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002259A2 (en) * | 1977-12-01 | 1979-06-13 | The Wellcome Foundation Limited | Hydantoin derivatives and salts thereof, their synthesis and pharmaceutical formulations |
| US4189587A (en) * | 1977-04-05 | 1980-02-19 | Ciba-Geigy Corporation | 1,3-Diaminomethyl-hydantoin additives for lubricating oils |
| US4944791A (en) * | 1982-04-08 | 1990-07-31 | Shell Internationale Research Maatschappij B.V. | Herbicidal hydantoins |
-
1956
- 1956-12-14 GB GB3819856A patent/GB817745A/en not_active Expired
Cited By (4)
| 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 |
| EP0002259A2 (en) * | 1977-12-01 | 1979-06-13 | The Wellcome Foundation Limited | Hydantoin derivatives and salts thereof, their synthesis and pharmaceutical formulations |
| EP0002259B1 (en) * | 1977-12-01 | 1984-10-03 | The Wellcome Foundation Limited | Hydantoin derivatives and salts thereof, their synthesis and pharmaceutical formulations |
| US4944791A (en) * | 1982-04-08 | 1990-07-31 | Shell Internationale Research Maatschappij B.V. | Herbicidal hydantoins |
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