JPS5492961A - Production of 5-arylhydantoin - Google Patents
Production of 5-arylhydantoinInfo
- Publication number
- JPS5492961A JPS5492961A JP15778377A JP15778377A JPS5492961A JP S5492961 A JPS5492961 A JP S5492961A JP 15778377 A JP15778377 A JP 15778377A JP 15778377 A JP15778377 A JP 15778377A JP S5492961 A JPS5492961 A JP S5492961A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formula
- aryl
- reaction
- medium
- 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.)
- Granted
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 2
- 239000002609 medium Substances 0.000 abstract 2
- 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
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 229960002449 glycine Drugs 0.000 abstract 1
- 229960004275 glycolic acid Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PURPOSE: Title compound useful as an intermediate of α-aryl-α-aminoacetic acid (a modifier of semisynthetic penicillin) is efficiently produced from safe and industrially available α-aryl-α-hydroxyacetic acid or its precursor and urea.
CONSTITUTION: The reaction of α-aryl-α-hydroxyacetic acid as p-hydroxymandelic acid of formula I (R1 is p- or o-substituted OH, 1W6C alkoxy or alkyl, halogen, acylated amino, NO2) with urea in an amount of preferably 2W10 times the molar quantity of the hydroxyacetic acid is conducted in an acidic medium, preferably aqueous sulfuric or hydrochloric acid medium, much preferably 5W25% concentration of sulfuric or hydrochloric acid to produce 5-arylhydantoin of formula II. The compound of formula I is prepared by reaction of glyoxylic acid with a compound of formula III in an alkaline aqueous medium and the product can be used for the subsequent reaction without the isolation of the comound of formula I.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15778377A JPS5492961A (en) | 1977-12-29 | 1977-12-29 | Production of 5-arylhydantoin |
| GB7850228A GB2012756B (en) | 1977-12-29 | 1978-12-29 | Process for preparing 5-arylhydantoins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15778377A JPS5492961A (en) | 1977-12-29 | 1977-12-29 | Production of 5-arylhydantoin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5492961A true JPS5492961A (en) | 1979-07-23 |
| JPS5757033B2 JPS5757033B2 (en) | 1982-12-02 |
Family
ID=15657192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15778377A Granted JPS5492961A (en) | 1977-12-29 | 1977-12-29 | Production of 5-arylhydantoin |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5492961A (en) |
| GB (1) | GB2012756B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4457939A (en) * | 1982-11-01 | 1984-07-03 | Pfizer Inc. | Aldose reductase inhibiting 5-(2-alkoxy-3-substituted phenyl)hydantoins |
| EP0112620B1 (en) * | 1982-11-01 | 1986-12-30 | Pfizer Inc. | 5-(substituted phenyl) hydantoins |
| ES2018743A6 (en) * | 1989-11-29 | 1991-05-01 | Etilo Derivados | Preparing 5-(4-hydroxyphenyl)hydantoin |
| JP2974742B2 (en) * | 1990-09-04 | 1999-11-10 | 鐘淵化学工業株式会社 | Method for producing 5-arylhydantoins |
| AT398199B (en) * | 1992-11-27 | 1994-10-25 | Chemie Linz Gmbh | METHOD FOR PRODUCING ARYLHYDANTOINES |
| DE59905623D1 (en) | 1998-09-22 | 2003-06-26 | Degussa | Process for the preparation of imidazolidine-2,4-diones |
Citations (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 |
-
1977
- 1977-12-29 JP JP15778377A patent/JPS5492961A/en active Granted
-
1978
- 1978-12-29 GB GB7850228A patent/GB2012756B/en not_active Expired
Patent Citations (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5757033B2 (en) | 1982-12-02 |
| GB2012756B (en) | 1982-06-30 |
| GB2012756A (en) | 1979-08-01 |
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