DE4037368A1 - Verfahren zur herstellung des 5-(4-hydroxyphenyl)-hydantoins - Google Patents
Verfahren zur herstellung des 5-(4-hydroxyphenyl)-hydantoinsInfo
- Publication number
- DE4037368A1 DE4037368A1 DE4037368A DE4037368A DE4037368A1 DE 4037368 A1 DE4037368 A1 DE 4037368A1 DE 4037368 A DE4037368 A DE 4037368A DE 4037368 A DE4037368 A DE 4037368A DE 4037368 A1 DE4037368 A1 DE 4037368A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyphenyl
- hydantoin
- formula
- mol
- acid
- 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.)
- Ceased
Links
- UMTNMIARZPDSDI-UHFFFAOYSA-N 5-(4-hydroxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1C1C(=O)NC(=O)N1 UMTNMIARZPDSDI-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 14
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229960004275 glycolic acid Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- KLLNNOKGNSIGHX-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxyphenyl)acetic acid Chemical compound OC1=CC=C(C(C(=O)O)O)C=C1.OC1=CC=C(C=C1)C(C(=O)O)O KLLNNOKGNSIGHX-UHFFFAOYSA-N 0.000 description 1
- KDNVHMPPUPGRQS-UHFFFAOYSA-N 3-hydroxy-2-(4-hydroxyphenyl)propanoic acid Chemical compound OCC(C(O)=O)C1=CC=C(O)C=C1 KDNVHMPPUPGRQS-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
- 229930182555 Penicillin Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- -1 α- (4-hydroxyphenyl) -α-hydroxy-acetylacetate Chemical compound 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8904086A ES2018743A6 (es) | 1989-11-29 | 1989-11-29 | Un procedimiento para la preparacion de 5-(4-hidroxifenil) hidantoina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4037368A1 true DE4037368A1 (de) | 1991-06-06 |
Family
ID=8265082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4037368A Ceased DE4037368A1 (de) | 1989-11-29 | 1990-11-23 | Verfahren zur herstellung des 5-(4-hydroxyphenyl)-hydantoins |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT399150B (fr) |
| DE (1) | DE4037368A1 (fr) |
| ES (1) | ES2018743A6 (fr) |
| FR (1) | FR2655041B1 (fr) |
| GB (1) | GB2238543B (fr) |
| IT (1) | IT1243927B (fr) |
| NL (1) | NL9002609A (fr) |
| PT (1) | PT96002B (fr) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2012756A (en) * | 1977-12-29 | 1979-08-01 | Ajinomoto Kk | Preparation of 5-arylhydantoins |
| EP0008547A1 (fr) * | 1978-08-03 | 1980-03-05 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé de fabrication de la R.S. p-hydroxyphényl-5 imidazolidinedione-2,4 ou R.S. p-hydroxyphényl-5 hydantoine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001319A1 (fr) * | 1977-08-18 | 1979-04-04 | Beecham Group Plc | Procédé de préparation de l'hydroxyphénylhydantoine et de l'hydroxyphénylglycine et composés ainsi obtenus |
-
1989
- 1989-11-29 ES ES8904086A patent/ES2018743A6/es not_active Expired - Lifetime
-
1990
- 1990-11-20 GB GB9025233A patent/GB2238543B/en not_active Expired - Fee Related
- 1990-11-23 DE DE4037368A patent/DE4037368A1/de not_active Ceased
- 1990-11-23 FR FR9014659A patent/FR2655041B1/fr not_active Expired - Fee Related
- 1990-11-23 IT IT02218390A patent/IT1243927B/it active IP Right Grant
- 1990-11-26 AT AT0239690A patent/AT399150B/de not_active IP Right Cessation
- 1990-11-27 PT PT96002A patent/PT96002B/pt not_active IP Right Cessation
- 1990-11-29 NL NL9002609A patent/NL9002609A/nl not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2012756A (en) * | 1977-12-29 | 1979-08-01 | Ajinomoto Kk | Preparation of 5-arylhydantoins |
| EP0008547A1 (fr) * | 1978-08-03 | 1980-03-05 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé de fabrication de la R.S. p-hydroxyphényl-5 imidazolidinedione-2,4 ou R.S. p-hydroxyphényl-5 hydantoine |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis 1981, S. 807-809 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2238543B (en) | 1993-01-06 |
| ES2018743A6 (es) | 1991-05-01 |
| PT96002A (pt) | 1991-09-13 |
| GB2238543A (en) | 1991-06-05 |
| FR2655041A1 (fr) | 1991-05-31 |
| IT1243927B (it) | 1994-06-28 |
| IT9022183A0 (it) | 1990-11-23 |
| NL9002609A (nl) | 1991-06-17 |
| AT399150B (de) | 1995-03-27 |
| PT96002B (pt) | 1998-01-30 |
| IT9022183A1 (it) | 1991-05-30 |
| GB9025233D0 (en) | 1991-01-02 |
| FR2655041B1 (fr) | 1993-08-20 |
| ATA239690A (de) | 1994-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |