GB764146A - Production of new hydantoin derivatives - Google Patents
Production of new hydantoin derivativesInfo
- Publication number
- GB764146A GB764146A GB3497/55A GB349755A GB764146A GB 764146 A GB764146 A GB 764146A GB 3497/55 A GB3497/55 A GB 3497/55A GB 349755 A GB349755 A GB 349755A GB 764146 A GB764146 A GB 764146A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- carboxylic acid
- ethyl
- butyl
- ester
- 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
- 150000001469 hydantoins Chemical class 0.000 title abstract 2
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title 1
- -1 methyl - iso - butyl Chemical group 0.000 abstract 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 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 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- MNQUHSLUIRMKFR-UHFFFAOYSA-N ethyl 1-(ethoxycarbonylamino)cyclohexane-1-carboxylate Chemical compound CCOC(=O)NC1(C(=O)OCC)CCCCC1 MNQUHSLUIRMKFR-UHFFFAOYSA-N 0.000 abstract 1
- KUAFMPWKUNNUEC-UHFFFAOYSA-N ethyl 1-aminocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1(N)CCCCC1 KUAFMPWKUNNUEC-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000006178 methyl benzyl group Chemical group 0.000 abstract 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000003944 tolyl group Chemical group 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises hydantoins of the general formula <FORM:0764146/IV(b)/1> where R1 and R2 are the same or different hydrocarbon radicals, any aliphatic chains of which can be interrupted by O or S and/or any aromatic nuclei of which can be halogen or alkoxy substituted, and which can be linked to each other, and their preparation by heating the dihydrazide or an ester of a monohydrazide of a C,C-disubstituted glycine-N-carboxylic acid in the presence or absence of solvents or diluents. A specific diluent is water, this being gradually distilled off to remove continuously the liberated hydrazine. Examples describe the preparation, by heating a di-lower alkyl ester of the appropriate C,C-disubstituted glycine-N-carboxylic acid with excess hydrazine hydrate in absolute ethanol or methanol, distilling off the solvent and concentrating an aqueous solution of the dihydrazide residue by heating, of the following compounds of the above general formula in which R1 and R2 in the same compound have the values: dimethyl, methyl - iso - butyl, diethyl, ethyl - n - butyl, methyl-n-hexyl, pentamethylene, and methylbenzyl. The following 5,5-disubstituted-3-amino hydantions are also referred to: methylethyl, methyl-n-propyl, ethyl-n-amyl, methylcyclopropyl, methyl - phenyl, ethyl - phenyl, diphenyl, methyl - allyl, ethyl - cyclohexenyl, methyl - p - chlorophenyl, methyl - p - methoxyphenyl, methyl - b - phenoxyethyl, methylb -methylmercaptoethyl and methyl-sec-butyl. Starting material. N-carbethoxy-1-aminocyclohexane carboxylic acid ethyl ester is obtained by reacting 1-amino-cyclohexane carboxylic acid ethyl ester with chloroformic acid ethyl ester.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL764146X | 1954-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB764146A true GB764146A (en) | 1956-12-19 |
Family
ID=11056238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3497/55A Expired GB764146A (en) | 1954-02-16 | 1955-02-07 | Production of new hydantoin derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB764146A (en) |
-
1955
- 1955-02-07 GB GB3497/55A patent/GB764146A/en not_active Expired
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