DE275833C - - Google Patents
Info
- Publication number
- DE275833C DE275833C DENDAT275833D DE275833DA DE275833C DE 275833 C DE275833 C DE 275833C DE NDAT275833 D DENDAT275833 D DE NDAT275833D DE 275833D A DE275833D A DE 275833DA DE 275833 C DE275833 C DE 275833C
- Authority
- DE
- Germany
- Prior art keywords
- carbazole
- acetic acid
- glacial acetic
- mixture
- nitric 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.)
- Active
Links
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 229960000583 Acetic Acid Drugs 0.000 claims description 10
- 239000012362 glacial acetic acid Substances 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- -1 mononitrodichlorocarbazole Chemical compound 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZGDRLAHGFSGLRI-UHFFFAOYSA-N 1,2-dichloro-9H-carbazole Chemical compound C1=CC=C2C3=CC=C(Cl)C(Cl)=C3NC2=C1 ZGDRLAHGFSGLRI-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- IEMXKVCEQAQLOJ-UHFFFAOYSA-N 1,2-dibromo-9H-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C(Br)=C3NC2=C1 IEMXKVCEQAQLOJ-UHFFFAOYSA-N 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- AYGIDQPCZBWJMY-UHFFFAOYSA-N BrC1=C(C(=C(C=2NC3=CC=CC=C3C1=2)[N+](=O)[O-])[N+](=O)[O-])Br Chemical compound BrC1=C(C(=C(C=2NC3=CC=CC=C3C1=2)[N+](=O)[O-])[N+](=O)[O-])Br AYGIDQPCZBWJMY-UHFFFAOYSA-N 0.000 description 1
- IXFVCUCZGFPDDO-UHFFFAOYSA-N ClC=1C(=C(C=2NC3=CC=CC=C3C=2C=1)[N+](=O)[O-])Cl Chemical compound ClC=1C(=C(C=2NC3=CC=CC=C3C=2C=1)[N+](=O)[O-])Cl IXFVCUCZGFPDDO-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- YHVJDSYRPVJTMJ-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=C(C=2NC3=CC=CC=C3C1=2)Cl)Cl)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=C(C(=C(C=2NC3=CC=CC=C3C1=2)Cl)Cl)[N+](=O)[O-] YHVJDSYRPVJTMJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE275833C true DE275833C (zh) |
Family
ID=532088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT275833D Active DE275833C (zh) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE275833C (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748541C (de) * | 1941-04-23 | 1944-11-06 | Verfahren zur Herstellung von chlorierten 3,6-Dinitrocharbazolen |
-
0
- DE DENDAT275833D patent/DE275833C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748541C (de) * | 1941-04-23 | 1944-11-06 | Verfahren zur Herstellung von chlorierten 3,6-Dinitrocharbazolen |
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