DE2546656A1 - Verfahren zur herstellung von hydrazobenzolderivaten - Google Patents
Verfahren zur herstellung von hydrazobenzolderivatenInfo
- Publication number
- DE2546656A1 DE2546656A1 DE19752546656 DE2546656A DE2546656A1 DE 2546656 A1 DE2546656 A1 DE 2546656A1 DE 19752546656 DE19752546656 DE 19752546656 DE 2546656 A DE2546656 A DE 2546656A DE 2546656 A1 DE2546656 A1 DE 2546656A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- sodium
- parts
- mixture
- aqueous
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical class NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 title description 6
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 241000282979 Alces alces Species 0.000 claims 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 20
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 15
- 235000019345 sodium thiosulphate Nutrition 0.000 description 15
- 238000001035 drying Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000004133 Sodium thiosulphate Substances 0.000 description 4
- OORGGNYDIUQRDG-UHFFFAOYSA-N [3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]-[3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]imino-oxidoazanium Chemical compound O1C(=O)C=2C(C)=CSC=2N=C1CC(C=C1)=CC=C1C(=O)C(C=1)=CC=CC=1N=[N+]([O-])C(C=1)=CC=CC=1C(=O)C(C=C1)=CC=C1CC(OC1=O)=NC2=C1C(C)=CS2 OORGGNYDIUQRDG-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 4
- BVPHWSDABGXRQD-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)hydrazine Chemical compound C1=CC(Cl)=CC=C1NNC1=CC=C(Cl)C=C1 BVPHWSDABGXRQD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- KVJYJSHGAOIUAH-UHFFFAOYSA-N (2-methoxyphenyl)-(2-methoxyphenyl)imino-oxidoazanium Chemical compound COC1=CC=CC=C1N=[N+]([O-])C1=CC=CC=C1OC KVJYJSHGAOIUAH-UHFFFAOYSA-N 0.000 description 2
- OVZJNFMCLJEZQV-UHFFFAOYSA-N 1,2-bis(2-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC=C1NNC1=CC=CC=C1OC OVZJNFMCLJEZQV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- NKUNBLUACJUHOA-UHFFFAOYSA-N (2-chlorophenyl)-(2-chlorophenyl)imino-oxidoazanium Chemical compound C=1C=CC=C(Cl)C=1[N+]([O-])=NC1=CC=CC=C1Cl NKUNBLUACJUHOA-UHFFFAOYSA-N 0.000 description 1
- ROMBIGIVDIQGKC-UHFFFAOYSA-N (2-methylphenyl)-(2-methylphenyl)imino-oxidoazanium Chemical compound CC1=CC=CC=C1N=[N+]([O-])C1=CC=CC=C1C ROMBIGIVDIQGKC-UHFFFAOYSA-N 0.000 description 1
- SXCDGVDBGGCCLV-UHFFFAOYSA-N (3-chlorophenyl)-(3-chlorophenyl)imino-oxidoazanium Chemical compound C=1C=CC(Cl)=CC=1[N+]([O-])=NC1=CC=CC(Cl)=C1 SXCDGVDBGGCCLV-UHFFFAOYSA-N 0.000 description 1
- DNZMYLLBWKOXQJ-UHFFFAOYSA-N 1,2-bis(2,5-dichlorophenyl)hydrazine Chemical compound ClC1=CC=C(Cl)C(NNC=2C(=CC=C(Cl)C=2)Cl)=C1 DNZMYLLBWKOXQJ-UHFFFAOYSA-N 0.000 description 1
- OVXBYJMCICSXFP-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NNC1=CC=CC=C1C OVXBYJMCICSXFP-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 241000159606 Netrium Species 0.000 description 1
- 241000862969 Stella Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical compound [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- -1 compounds Sodium hydroxide Chemical class 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
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 |
|---|---|---|---|
| FR7506858A FR2302998A1 (fr) | 1975-03-05 | 1975-03-05 | Procede de preparation de derives de l'hydrazobenzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2546656A1 true DE2546656A1 (de) | 1977-04-21 |
Family
ID=9152134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752546656 Withdrawn DE2546656A1 (de) | 1975-03-05 | 1975-10-17 | Verfahren zur herstellung von hydrazobenzolderivaten |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT338759B (enExample) |
| BE (1) | BE832268A (enExample) |
| CH (1) | CH593922A5 (enExample) |
| DE (1) | DE2546656A1 (enExample) |
| FR (1) | FR2302998A1 (enExample) |
| GB (1) | GB1546087A (enExample) |
| LU (1) | LU72308A1 (enExample) |
| NL (1) | NL7506019A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609530C2 (de) * | 1976-03-08 | 1983-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Hydrazobenzolen |
| CN1295209C (zh) * | 2005-07-14 | 2007-01-17 | 辽宁大学 | 一种合成氢化偶氮类化合物的方法 |
-
1975
- 1975-03-05 FR FR7506858A patent/FR2302998A1/fr active Granted
- 1975-04-17 LU LU72308A patent/LU72308A1/xx unknown
- 1975-05-22 NL NL7506019A patent/NL7506019A/xx not_active Application Discontinuation
- 1975-07-16 AT AT548475A patent/AT338759B/de not_active IP Right Cessation
- 1975-08-08 BE BE159063A patent/BE832268A/xx unknown
- 1975-10-17 DE DE19752546656 patent/DE2546656A1/de not_active Withdrawn
- 1975-10-24 CH CH1382275A patent/CH593922A5/xx not_active IP Right Cessation
-
1976
- 1976-05-19 GB GB1681275A patent/GB1546087A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA548475A (de) | 1977-01-15 |
| CH593922A5 (enExample) | 1977-12-30 |
| LU72308A1 (enExample) | 1976-03-17 |
| GB1546087A (en) | 1979-05-16 |
| FR2302998A1 (fr) | 1976-10-01 |
| FR2302998B1 (enExample) | 1978-06-23 |
| AT338759B (de) | 1977-09-12 |
| BE832268A (fr) | 1976-02-09 |
| NL7506019A (nl) | 1976-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |