DE1229080B - Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives - Google Patents
Process for the preparation of 2-methylmercapto-indandione (1, 3) derivativesInfo
- Publication number
- DE1229080B DE1229080B DER38122A DER0038122A DE1229080B DE 1229080 B DE1229080 B DE 1229080B DE R38122 A DER38122 A DE R38122A DE R0038122 A DER0038122 A DE R0038122A DE 1229080 B DE1229080 B DE 1229080B
- Authority
- DE
- Germany
- Prior art keywords
- methylmercapto
- indandione
- water
- derivatives
- preparation
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
C07cC07c
Deutsche KL: 12 ο-25German KL: 12 o-25
Nummer: 1 229 080Number: 1 229 080
Aktenzeichen: R38122IVb/12oFile number: R38122IVb / 12o
Anmeldetag: 12. Juni 1964Filing date: June 12, 1964
Auslegetag: 24. November 1966Opening day: November 24, 1966
Aus »Berichte der Deutschen Chemischen Gesellschaft«, 69, 1612 (1936), und H ο u b e η — Weyl, »Methoden der organischen Chemie«, Bd. 9, 204 (1955), ist es bekannt, daß α-Halogenthioäther in Gegenwart von Wasser zu Mercaptalen hydrolysiert werden.From "Reports of the German Chemical Society", 69, 1612 (1936), and H ο u b e η - Weyl, "Methods of organic chemistry", Vol. 9, 204 (1955), it is known that α-halogen thioethers in The presence of water can be hydrolyzed to mercaptals.
Weiterhin ist aus Journal of Organic Chemistry, 28, 1896 (1963), bekannt, daß die Hydrolyse von 2-Chlor-2-methylmercapto-indandion-(l,3) zu Ninhydrin führt, ohne daß die Zwischenstufe des 2-Hydroxy-2-methylmercapto-indandions-(l,3) gefaßt werden konnte.It is also known from Journal of Organic Chemistry, 28, 1896 (1963) that the hydrolysis of 2-chloro-2-methylmercapto-indandione- (l, 3) leads to ninhydrin without the intermediate stage of 2-hydroxy-2-methylmercapto-indandione- (l, 3) could be grasped.
überraschenderweise wurde nun gefunden, daß man 2-Chlor- bzw. 2-Brom- und 2-Methylmercaptoindandion-(l,3) auch zu den entsprechenden HaIbmercaptalen umsetzen kann.Surprisingly, it has now been found that 2-chloro- or 2-bromo- and 2-methylmercaptoindanedione (l, 3) can also implement to the corresponding Halbmercaptalen.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 2-Methylmercapto-indandion-(l,3)-derivaten der allgemeinen FormelThe invention relates to a process for the preparation of 2-methylmercapto-indandione (1,3) derivatives the general formula
in der R eine Hydroxy- oder Acyloxygruppe bedeutet, dadurch gekennzeichnet, daß man 2-Chlor- oder 2-Brom-2-methylmercapto-indandion-(l,3) bei erhöhter Temperatur mit Wasser oder mit einer Carbonsäure und deren Salz behandelt bzw. das erhaltene 2-Hydroxy-2-methylmercapto-indandion-(l,3) in üblicher Weise acyliert.in which R is a hydroxy or acyloxy group, characterized in that 2-chlorine or 2-Bromo-2-methylmercapto-indandione- (l, 3) at elevated temperature with water or with a carboxylic acid and the salt thereof treated or the 2-hydroxy-2-methylmercapto-indandione- (l, 3) obtained in the usual way Acylated way.
Als Reaktionstemperatur ist besonders zweckmäßig eine solche zwischen 90 und 1300C.A particularly expedient reaction temperature is between 90 and 130 ° C.
Die Verfahrensprodukte stellen bisher unbekannte, wertvolle Zwischenprodukte zur Herstellung von Farbstoffen, Arzneimitteln und Schädlingsbekämpfungsmitteln sowie Reagenzien dar.The process products represent previously unknown, valuable intermediate products for the production of Dyes, pharmaceuticals and pesticides as well as reagents.
35,5 g 2-Chlor-2-methylmercapto-indandion-(l,3) werden in 250 ml Wasser suspendiert und unter mechanischem Rühren 2 Stunden unter- Rückfluß erhitzt. Die erhaltene Reaktionsmischung wird heiß vom Ungelösten abgetrennt, mit Kohle geklärt, eingeengt und der Kristallisation überlassen. Nach Umkristallisieren aus Wasser erhält man 16,4 g Verfahren zur Herstellung35.5 g of 2-chloro-2-methylmercapto-indandione- (l, 3) are suspended in 250 ml of water and under Mechanical stirring heated under reflux for 2 hours. The reaction mixture obtained becomes hot separated from the undissolved material, clarified with charcoal, concentrated and left to crystallize. To Recrystallization from water gives 16.4 g of manufacturing process
von 2-Methylmercapto-indandion-(l,3)-derivateriof 2-methylmercapto-indandione- (1,3) -derivateri
Anmelder:Applicant:
Riedel-de-Haen Aktiengesellschaft,Riedel-de-Haen Aktiengesellschaft,
Seelze, Wunstorfer Str. 40Seelze, Wunstorfer Str. 40
Als Erfinder benannt:
Dr.-Ing. Horst Liebig,
Dr. rer. nat. Heinrich Pfetzing, Bad Nenndorf --Named as inventor:
Dr.-Ing. Horst Liebig,
Dr. rer. nat. Heinrich Pfetzing, Bad Nenndorf -
(51,4% der Theorie) 2-Hydroxy-2-methylmercaptoindandion-(l,3). F. 120,5 bis 121,5°C.(51.4% of theory) 2-Hydroxy-2-methylmercaptoindanedione- (1.3). M.p. 120.5 to 121.5 ° C.
Analyse: Ci0H8O3S (208,23).Analysis: Ci 0 H 8 O 3 S (208.23).
Berechnet ... C 57,7, H 3,87, S 15,4%;
gefunden ... C 57,2, H 3,9, S 15,45%.Calculated ... C 57.7, H 3.87, S 15.4%;
Found ... C 57.2, H 3.9, S 15.45%.
45,4 g 2-Chlor-2-methylmercapto-indandion-(l,3) werden in 125 ml Eisessig gelöst, mit 18 g wasserfreiem Na-Acetat versetzt und 20 Minuten unter Rückfluß erhitzt. Die sich beim Erkalten der Lösung bildenden Kristalle werden abgesaugt und mit Eisessig gewaschen. Ausbeute: 41,5 g (82,5% der Theorie) 2-Acetoxy-2-methylmercapto-indandion-(l,3).45.4 g of 2-chloro-2-methylmercapto-indandione- (l, 3) are dissolved in 125 ml of glacial acetic acid, with 18 g of anhydrous Na acetate is added and the mixture is heated under reflux for 20 minutes. When the solution cools down Crystals that form are filtered off with suction and washed with glacial acetic acid. Yield: 41.5 g (82.5% of theory) 2-acetoxy-2-methylmercapto-indandione- (1,3).
Durch Verdünnen der Mutterlauge mit Wasser erhält man weitere 7,8 g (15,5% der Theorie).By diluting the mother liquor with water, a further 7.8 g (15.5% of theory) are obtained.
Nach Umkristallisieren aus Methanol schmilzt das Produkt bei 137,5 bis 139°C.After recrystallization from methanol, the product melts at 137.5 to 139 ° C.
Analyse: Ci2Hi0O4S (250,27).Analysis: Ci 2 Hi 0 O 4 S (250.27).
Berechnet ... C 57,59, H 4,03, S 12,81%;
gefunden ... C 57,1, H 4,1, S 12,7%.Calculated ... C 57.59, H 4.03, S 12.81%;
Found ... C 57.1, H 4.1, S 12.7%.
2,5 g des nach Beispiel 1 erhaltenen 2-Hydroxy-2-methylmercapto-indandions-(l,3) werden in 5 ml trockenem Pyridin gelöst und mit 5 ml Acetanhydrid versetzt. Nach mehrstündigem Stehen bei Raumtemperatur gießt man die Reaktionslösung in 50 ml Eiswasser. Die ausgeschiedenen Kristalle werden abgesaugt und mit Wasser gewaschen. Ausbeute: 2,7 g (90% der Theorie) 2-Acetoxy-2-methylmercaptoindandion-(l,3). 2.5 g of the 2-hydroxy-2-methylmercapto-indandione (l, 3) obtained according to Example 1 are dissolved in 5 ml of dry pyridine and treated with 5 ml of acetic anhydride. After standing for several hours at room temperature the reaction solution is poured into 50 ml of ice water. The precipitated crystals are filtered off with suction and washed with water. Yield: 2.7 g (90% of theory) of 2-acetoxy-2-methylmercaptoindanedione- (1.3).
Nach Umkristallisieren aus Methanol schmilzt das Produkt bei 137,5 bis 139° C.After recrystallization from methanol, the product melts at 137.5 to 139 ° C.
609 72a/427609 72a / 427
Nach dem IR-Spektrum und der Analyse erweist es sich identisch mit dem Produkt aus Beispiel 2.According to the IR spectrum and the analysis, it turns out to be identical to the product from Example 2.
Analyse: Ci2Hi0O4S (250,27).
Berechnet ... C 57,6, H 4,0, S 12,8%; ,Analysis: Ci 2 Hi 0 O 4 S (250.27).
Calculated ... C 57.6, H 4.0, S 12.8%; ,
gefunden ... C 57,1, H 4,1, S 12,7%.Found ... C 57.1, H 4.1, S 12.7%.
66 g Phthalsäurediäthylester werden in 113 ml trockenem Dimethylsulfoxyd gelöst und mit 16,2 g Natriummethylat versetzt. Nach 4 Stunden Rühren unter Stickstoffatmosphäre bei 400C wird die Hauptmenge an Dimethylsulfoxyd im Vakuum abdestilliert. Der viskose Rückstand wird in 75 ml Eiswasser aufgenommen, zweimal mit je 40 ml Äther gewaschen und dann in ein Gemisch aus 90 ml Wasser und 150 ml 40%iger Bromwasserstoffsäure eingetragen. Man erhält 30,0 g kristallines Rohprodukt. Nach Umkristallisation aus Diäthyläther erhält man reines 2-Brom-2-methylmercapto-indandion-(1,3) vom Schmelzpunkt 82 bis 82,5 0C.66 g of diethyl phthalate are dissolved in 113 ml of dry dimethyl sulfoxide, and 16.2 g of sodium methylate are added. After stirring for 4 hours under a nitrogen atmosphere at 40 ° C., the majority of dimethyl sulfoxide is distilled off in vacuo. The viscous residue is taken up in 75 ml of ice water, washed twice with 40 ml of ether each time and then added to a mixture of 90 ml of water and 150 ml of 40% hydrobromic acid. 30.0 g of crystalline crude product are obtained. After recrystallization from diethyl ether gives pure 2-bromo-2-methylmercapto-indandion- (1,3) of melting point 82 to 82.5 0 C.
Analyse: Ci0H7O2SBr (271,13).Analysis: Ci 0 H 7 O 2 SBr (271.13).
Berechnet... C 44,30, H 2,60, S 11,82, Br 29,47%; gefunden ... C 44,4, H 2,7, S 11,8, Br 29,3%. 2J Calculated ... C 44.30, H 2.60, S 11.82, Br 29.47%; found ... C 44.4, H 2.7, S 11.8, Br 29.3%. 2Y
5 g2-Brom-2-methylmercapto-indandion-(l,3) werden in 14 ml Eisessig gelöst, mit 2 g wasserfreiem Natriumacetat versetzt und 20 Minuten unter Rückfluß erhitzt. Die sich beim Erkalten der Lösung bildenden Kristalle werden abgesaugt und mit Eisessig gewaschen. Man erhält 2,9 g (62,8% derTheorie) 2-Acetoxy-2-methylmercapto-indandion-(l,3). Nach Umkristallisation aus Methanol schmilzt das Produkt bei 137,5 bis 139°C.5 g of 2-bromo-2-methylmercapto-indandione- (l, 3) are dissolved in 14 ml of glacial acetic acid, with 2 g of anhydrous Sodium acetate is added and the mixture is heated under reflux for 20 minutes. When the solution cools down Crystals that form are filtered off with suction and washed with glacial acetic acid. 2.9 g (62.8% of theory) are obtained 2-acetoxy-2-methylmercapto-indandione- (1,3). After recrystallization from methanol, the product melts at 137.5 to 139 ° C.
Nach Schmelzpunkt und IR-Spektrum erweist sich die Substanz identisch mit dem Produkt aus Beispiel 2.According to the melting point and IR spectrum, the substance proves to be identical to the product from Example 2.
Beispiel 5 .Example 5.
17,8 g 2-Chlor-2-methylmercapto-indandion-(l,3) werden in 49 ml Ameisensäure gelöst, mit 5,9 g Natriumformiat versetzt und etwa 5 Minuten unter Rückfluß erhitzt. Nach dem Abkühlen wird mit Eiswasser versetzt, bis vollständige Kristallisation eintritt. Nach Isolierung wird das Produkt durch Umkristallisation aus Methanol gereinigt. Ausbeute: 12,3g2-Formyloxy-2-methylmercapto-indandion-(l,3) (= 66,2% der Theorie), Fp. 135 bis 136°C.17.8 g of 2-chloro-2-methylmercapto-indandione- (l, 3) are dissolved in 49 ml of formic acid, with 5.9 g Sodium formate is added and the mixture is refluxed for about 5 minutes. After cooling, it is poured with ice water added until complete crystallization occurs. After isolation, the product is obtained by recrystallization purified from methanol. Yield: 12,3g2-formyloxy-2-methylmercapto-indandione- (1,3) (= 66.2% of theory), melting point 135 to 136 ° C.
Analyse: CuH8O4S (236,24).
Berechnet... C 55,91, H 3,41, O 27,10, S 13,57%; gefunden ... C 55,68, H 3,46, O 26,32, S 13,5%.Analysis: CuH 8 O 4 S (236.24).
Calculated ... C 55.91, H 3.41, O 27.10, S 13.57%; Found ... C 55.68, H 3.46, O 26.32, S 13.5%.
5 g 2-Chlor-2-methylmercapto-indandion-(l,3) werden in einer Mischung von 14 ml Propionsäure und 0,97 g Natriumhydroxyd gelöst und 5 Minuten unter Rückfluß erhitzt. Die Reaktionslösung wird abgekühlt und mit Eis versetzt; dabei tritt eine anfangs ölige, dann jedoch kristalline Abscheidung auf. Nach Isolierung wird das Produkt zur Reinigung in wenig Methanol gelöst und nach dem Klären mit Kohle langsam mit Wasser wieder ausgefällt. Ausbeute: 5,3 g 2 - Propionoxy - 2 - methylmercapto - indandion - (1,3) (= 91% der Theorie), Fp. 57 bis 58°C.5 g of 2-chloro-2-methylmercapto-indandione (l, 3) are in a mixture of 14 ml of propionic acid and Dissolved 0.97 g of sodium hydroxide and refluxed for 5 minutes. The reaction solution is cooled and mixed with ice; an initially oily, but then crystalline deposit occurs. To Isolation, the product is dissolved in a little methanol for purification and after clarification with charcoal slowly reprecipitated with water. Yield: 5.3 g of 2 - propionoxy - 2 - methylmercapto - indanedione - (1.3) (= 91% of theory), melting point 57 to 58 ° C.
Analyse: Ci3Hi2O4S (264,29).Analysis: Ci 3 Hi 2 O 4 S (264.29).
Berechnet ... C 59,08, H 4,57, S 12,13%;
gefunden ... C 59,2, H 4,8, S 11,8%.Calculated ... C 59.08, H 4.57, S 12.13%;
Found ... C 59.2, H 4.8, S 11.8%.
In einem Gemisch von 20 ml Methanol und 10 ml Wasser werden 16,2 g Benzoesäure und 1,94 g Natriumhydroxyd gelöst und dann 10 g 2-Chlor-2-methylmercapto-indandion-(l,3) zugesetzt. Die Mischung wird etwa 10 Minuten unter Rückfluß gekocht und nach dem Abkühlen mit einem Überschuß an Wasser gefällt. Zur Entfernung von überschüssiger Benzoesäure wird der Niederschlag zweimal mit je 250 ml Wasser ausgekocht und der Rückstand aus Methanol umkristallisiert. Man erhält 3,8 g 2-Benzoyloxy-2-methylmercapto-indandion-(l,3) (= 27,5% der Theorie), Fp. 143 bis 144°C.In a mixture of 20 ml of methanol and 10 ml of water, 16.2 g of benzoic acid and 1.94 g of sodium hydroxide are added dissolved and then 10 g of 2-chloro-2-methylmercapto-indandione- (l, 3) added. The mixture is refluxed for about 10 minutes and, after cooling, with an excess like in water. The precipitate is used twice to remove excess benzoic acid Boiled with 250 ml of water each time and the residue is recrystallized from methanol. You get 3.8 g of 2-benzoyloxy-2-methylmercapto-indandione- (1.3) (= 27.5% of theory), melting point 143 to 144 ° C.
Analyse: Ci7Hi2O4S (312,35).
Berechnet... C 65,38, H 3,87, O 20,49, S 10,24%; gefunden ... C 65,1, H 4,0, O 19,5, S 11,1%.Analysis: Ci 7 Hi 2 O 4 S (312.35).
Calculated ... C 65.38, H 3.87, O 20.49, S 10.24%; Found ... C 65.1, H 4.0, O 19.5, S 11.1%.
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER38123A DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DER38122A DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DEP1270A DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
| CH681365A CH461472A (en) | 1964-06-12 | 1965-05-14 | Process for the production of ninhydrin |
| GB24588/65A GB1035180A (en) | 1964-06-12 | 1965-06-10 | Process for the preparation of ninhydrin |
| FR20546A FR1437103A (en) | 1964-06-12 | 1965-06-11 | Process for the preparation of ninhydrin |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER38123A DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DER38122A DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DEP1270A DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1229080B true DE1229080B (en) | 1966-11-24 |
Family
ID=27212157
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38122A Pending DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DER38123A Pending DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DEP1270A Pending DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38123A Pending DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DEP1270A Pending DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH461472A (en) |
| DE (3) | DE1229080B (en) |
| FR (1) | FR1437103A (en) |
| GB (1) | GB1035180A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385894A (en) * | 1965-06-30 | 1968-05-28 | Shulton Inc | Oxidation of activated methylene group containing compounds to the corresponding carbonyl compounds |
| CN108047018B (en) * | 2017-12-12 | 2022-07-22 | 上海三爱思试剂有限公司 | Synthetic method of ninhydrin |
-
1964
- 1964-06-12 DE DER38122A patent/DE1229080B/en active Pending
- 1964-06-12 DE DER38123A patent/DE1207381B/en active Pending
- 1964-06-19 DE DEP1270A patent/DE1270040B/en active Pending
-
1965
- 1965-05-14 CH CH681365A patent/CH461472A/en unknown
- 1965-06-10 GB GB24588/65A patent/GB1035180A/en not_active Expired
- 1965-06-11 FR FR20546A patent/FR1437103A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1437103A (en) | 1966-04-29 |
| DE1207381B (en) | 1965-12-23 |
| CH461472A (en) | 1968-08-31 |
| GB1035180A (en) | 1966-07-06 |
| DE1270040B (en) | 1968-06-12 |
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