CH169349A - Process for the preparation of 4-methyl-5-chloro-7-methoxyisatin-a-chloride. - Google Patents
Process for the preparation of 4-methyl-5-chloro-7-methoxyisatin-a-chloride.Info
- Publication number
- CH169349A CH169349A CH169349DA CH169349A CH 169349 A CH169349 A CH 169349A CH 169349D A CH169349D A CH 169349DA CH 169349 A CH169349 A CH 169349A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloride
- methyl
- methoxyisatin
- chloro
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- FGZDNNJCFOKWBL-UHFFFAOYSA-N 7-methoxy-4-methyl-1h-indole-2,3-dione Chemical compound COC1=CC=C(C)C2=C1NC(=O)C2=O FGZDNNJCFOKWBL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4-Nethyl-6-ehlor-7-methoxyisatin-a-ehlorid. Es wurde gefunden, dass man 4-Methyl- 5-chlor-7-methO'xyisatin-a-chlorid herstellen kann, wenn 4-Methyl-7-methoxyisatin-a-chlo- rid mit im Kerne chlorierenden Mitteln be handelt wird.
Die Behandlung des 4-Methyl-7-methoxy- isatin-a-chlorids mit den im Kerne chlorieren- den Mitteln kann in verschiedenster Weise, wie zum Beispiel in Gegenwart indifferenter Lösungs- oder Verdünnungsmittel, wie. bei spielsweise Benzol, Chlorbenzol, Nitrobenzol, Tetrachloräthan oder Chloroform, erfolgen.
Als im Kern chlorierende Mittel können beispielsweise Chlor oder Sulfurylchlorid in Gegenwart oder Abwesenheit. von Halogen überträgere, wie zum Beispiel Jod, Antimon pentachlorid .oder Eisen und dessen Salzen, verwendet werden; besonders gute Resultate in bezug auf die Ausbeuten an 4-Methyl-5- chlor-7-methoxyisatin-a-chlorid werden bei Verwendung von Sulfurylchlorid als chlorie- rendes Mittel erhalten.
<I>Beispiel:</I> 19,1 Teile 4-Methyl-7-methoxyisatin wer den durch halbstündiges Erwärmen auf 80 bis<B>85"</B> mit 22 Teilen PCh und 600 Teilen Chlorbenzol in das 4-Methyl-7-methogyisatin- a-chlorid übergeführt.- Zu der auf etwa 50 bis 55 erkalteten Lösung werden unter Rühren 14 Teile Sulfurylchlorid gegeben. Hierauf wird eine Stunde bei 60 - 65 ge halten.
Nach dieser Zeit ist die Chlorierung, die sich unter lebhafter Schwefeldioxydent- wicklung vollzieht, beendet. , Wird das Lösungsmittel, zum Beispiel durch Abdestillieren im Vakuum, grössenteils entfernt, so entsteht ein brauner Kristallbrei, der aus 4-Methyl-5-chlor-7-methoxyisatin-a- chlorid besteht; durch Abnutschen und Aus waschen mit etwas Petroläther kann das 4-Methyl-5 - chlor - 7 - methoxyisatiir - a - Chlorid isoliert werden.
In vielen Fällen ist ein Isolieren des für die Herstellung von Farbstoffen wertvollen 4-Methyl-5-chlor-7- metboxyisatin - a - chlorids nicht notwendig, sondern es kann ohne wei teres die Lösung oder Suspension des a-Chlo- rids verwendet werden, wie dies beispiels weise bei der Kondensation mit zur Herstel lung indigoider Farbstoffe geeigneten Kompo nenten möglich ist.
Process for the preparation of 4-methyl-6-chloro-7-methoxyisatin-a-chloride. It has been found that 4-methyl-5-chloro-7-methoxyisatin-a-chloride can be produced if 4-methyl-7-methoxyisatin-a-chloride is treated with agents that are chlorinating in the nucleus.
The treatment of the 4-methyl-7-methoxy-isatin-α-chloride with the agents chlorinating in the nucleus can be carried out in the most varied of ways, for example in the presence of inert solvents or diluents, such as. for example benzene, chlorobenzene, nitrobenzene, tetrachloroethane or chloroform take place.
Chlorinating agents in the core can be, for example, chlorine or sulfuryl chloride in the presence or absence. from halogen, such as iodine, antimony pentachloride .or iron and its salts, can be used; Particularly good results with regard to the yields of 4-methyl-5-chloro-7-methoxyisatin-α-chloride are obtained when using sulfuryl chloride as the chlorinating agent.
<I> Example: </I> 19.1 parts of 4-methyl-7-methoxyisatin are converted into 4-methyl by heating to 80 to <B> 85 "for half an hour with 22 parts of PCh and 600 parts of chlorobenzene -7-methogyisatin-a-chloride.- 14 parts of sulfuryl chloride are added with stirring to the solution, which has cooled to about 50 to 55. The temperature is then kept at 60-65 for one hour.
After this time the chlorination, which takes place with vigorous evolution of sulfur dioxide, is ended. If the solvent is largely removed, for example by distilling off in vacuo, a brown crystal paste is formed which consists of 4-methyl-5-chloro-7-methoxyisatin-a-chloride; the 4-methyl-5-chloro-7-methoxyizatiir-a-chloride can be isolated by suction filtration and washing out with a little petroleum ether.
In many cases, it is not necessary to isolate the 4-methyl-5-chloro-7-metboxyisatin - a - chloride, which is valuable for the production of dyes, but the solution or suspension of the a-chloride can be used without further ado. as is possible, for example, with condensation with components suitable for the production of indigoid dyes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH169349T | 1933-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169349A true CH169349A (en) | 1934-05-31 |
Family
ID=4421471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169349D CH169349A (en) | 1933-04-08 | 1933-04-08 | Process for the preparation of 4-methyl-5-chloro-7-methoxyisatin-a-chloride. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169349A (en) |
-
1933
- 1933-04-08 CH CH169349D patent/CH169349A/en unknown
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