SU854272A3 - Способ получени рацемического -окси-фЕНил- -гидАНТОиНА - Google Patents
Способ получени рацемического -окси-фЕНил- -гидАНТОиНА Download PDFInfo
- Publication number
- SU854272A3 SU854272A3 SU792790706A SU2790706A SU854272A3 SU 854272 A3 SU854272 A3 SU 854272A3 SU 792790706 A SU792790706 A SU 792790706A SU 2790706 A SU2790706 A SU 2790706A SU 854272 A3 SU854272 A3 SU 854272A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- hydantoin
- hydroxyphenyl
- mol
- monohydrate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000004202 carbamide Substances 0.000 claims abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 229940091173 hydantoin Drugs 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 11
- 150000004682 monohydrates Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 4
- -1 p-hydroxyphenyl Chemical group 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- CMKDJMDGRSJZIS-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carbaldehyde Chemical compound C1=CC=C2C(C=O)CCC2=C1 CMKDJMDGRSJZIS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DIRCLGLKRZLKHG-UHFFFAOYSA-N 4-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(O)C=C1 DIRCLGLKRZLKHG-UHFFFAOYSA-N 0.000 description 1
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7822989A FR2432510A1 (fr) | 1978-08-03 | 1978-08-03 | Procede de fabrication de la r.s p-hydroxyphenyl-5 imidazolidine-dione-2,4 ou r.s p-hydroxyphenyl-5 hydantoine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU854272A3 true SU854272A3 (ru) | 1981-08-07 |
Family
ID=9211563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792790706A SU854272A3 (ru) | 1978-08-03 | 1979-08-02 | Способ получени рацемического -окси-фЕНил- -гидАНТОиНА |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0008547B1 (enExample) |
| JP (1) | JPS5522691A (enExample) |
| AT (1) | ATE1778T1 (enExample) |
| DE (1) | DE2964015D1 (enExample) |
| ES (1) | ES483042A1 (enExample) |
| FR (1) | FR2432510A1 (enExample) |
| SU (1) | SU854272A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4301244A1 (de) * | 1993-01-19 | 1994-07-21 | Chemie Linz Deutschland | Verfahren zur Herstellung von Arylhydantoinen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2018743A6 (es) * | 1989-11-29 | 1991-05-01 | Etilo Derivados | Un procedimiento para la preparacion de 5-(4-hidroxifenil) hidantoina. |
| WO1991009020A2 (en) * | 1989-12-14 | 1991-06-27 | Hoechst Celanese Corporation | PRODUCTION OF 5-(4'-HYDROXYPHENYL)HYDANTOIN AND D-p-HYDROXYPHENYLGLYCINE FROM 4-HYDROXYACETOPHENONE |
| JP2974742B2 (ja) * | 1990-09-04 | 1999-11-10 | 鐘淵化学工業株式会社 | ５―アリールヒダントインの製造方法 |
| AT398199B (de) * | 1992-11-27 | 1994-10-25 | Chemie Linz Gmbh | Verfahren zur herstellung von arylhydantoinen |
| US7073815B2 (en) * | 2002-04-24 | 2006-07-11 | Graco Children's Products Inc. | Stroller with drop-down basket |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53116373A (en) * | 1977-03-18 | 1978-10-11 | Kanegafuchi Chem Ind Co Ltd | Preparation of 5-(4-hydroxyphenyl)hydantoin |
-
1978
- 1978-08-03 FR FR7822989A patent/FR2432510A1/fr active Granted
-
1979
- 1979-07-26 AT AT79400533T patent/ATE1778T1/de not_active IP Right Cessation
- 1979-07-26 EP EP79400533A patent/EP0008547B1/fr not_active Expired
- 1979-07-26 DE DE7979400533T patent/DE2964015D1/de not_active Expired
- 1979-08-01 ES ES483042A patent/ES483042A1/es not_active Expired
- 1979-08-01 JP JP9860179A patent/JPS5522691A/ja active Pending
- 1979-08-02 SU SU792790706A patent/SU854272A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4301244A1 (de) * | 1993-01-19 | 1994-07-21 | Chemie Linz Deutschland | Verfahren zur Herstellung von Arylhydantoinen |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE1778T1 (de) | 1982-11-15 |
| EP0008547A1 (fr) | 1980-03-05 |
| JPS5522691A (en) | 1980-02-18 |
| EP0008547B1 (fr) | 1982-11-10 |
| DE2964015D1 (en) | 1982-12-16 |
| FR2432510A1 (fr) | 1980-02-29 |
| FR2432510B1 (enExample) | 1981-01-30 |
| ES483042A1 (es) | 1980-05-16 |
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