GB869372A - Improvements relating to 4-nitrostyryl-2-sulphonic acid compounds - Google Patents
Improvements relating to 4-nitrostyryl-2-sulphonic acid compoundsInfo
- Publication number
- GB869372A GB869372A GB13375/58A GB1337558A GB869372A GB 869372 A GB869372 A GB 869372A GB 13375/58 A GB13375/58 A GB 13375/58A GB 1337558 A GB1337558 A GB 1337558A GB 869372 A GB869372 A GB 869372A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- sulphonic acid
- sulphonic
- aldehyde
- benzaldehyde
- 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.)
- Expired
Links
- -1 alkali metal salt Chemical class 0.000 abstract 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 3
- 238000004519 manufacturing process Methods 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract 1
- ZDTXQHVBLWYPHS-UHFFFAOYSA-N 4-nitrotoluene-2-sulfonic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O ZDTXQHVBLWYPHS-UHFFFAOYSA-N 0.000 abstract 1
- GTTBJBSBKJKGHC-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C=CC1=CC=CC=C1 GTTBJBSBKJKGHC-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052790 beryllium Inorganic materials 0.000 abstract 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005282 brightening Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004674 formic acids Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- WOHMODZLSWIUCL-UHFFFAOYSA-N n-(4-formyl-3-methoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1C=O WOHMODZLSWIUCL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- DMYJULZCXUJJJQ-UHFFFAOYSA-N pyridine-2-carbaldehyde;thiophene-2-carbaldehyde Chemical compound O=CC1=CC=CS1.O=CC1=CC=CC=N1 DMYJULZCXUJJJQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of 4-nitrostyryl-2-sulphonic acid-aryl compounds of the general formula: <FORM:0869372/IV (b)/1> wherein Ar represents an aromatic radical or heterocyclic radical of aromatic character is characterised by condensing at temperatures of over 100 DEG C., 4-nitro-1-methylbenzene-2-sulphonic acid in the form of an alkali metal salt, an alkaline earth metal salt or a salt with a saturated organic nitrogenous base which salt either melts or is soluble in organic solvents with an aromatic aldehyde or heterocyclic aldehyde of aromatic character in the presence of a saturated secondary base as condensing agent, the condensation preferably being performed in the presence of hydrophilic organic solvents. In a modification of the process the aldehyde may be used in the form of its condensation product with 2 mols of secondary amine. Examples of saturated organic nitrogenous bases specified are dimethylamine and piperidine. Solvents mentioned include amides of formic and acetic acids and saturated organic sulphones and formamide being preferred. Alkali metal and alkaline earth metal salts specified include sulphoxides, dimethyl sulphoxide and dimethyl those of lithium, sodium, potassium, beryllium and magnesium. Aldehydes employed in the process may contain as substituents halogen, alkyl, alkoxy, cyano, alkyl or aryl sulphone-, tertiary sulphonic acid amide, nitro, acylamino, sulphonic and dialkyl-amino groups, specific examples being benzaldehyde, 4-acetylamino-2-methoxy benzaldehyde, thiophene-2-aldehyde pyridine-2-aldehyde, benzaldehyde 2-sulphonic acid and p-dimethyl amino benzaldehyde, isophthaldehyde and terephthaldehyde. Examples Examples are furnished relating to the production of sodium salts of 4-nitrostilbene-2-sulphonic acid, 4-nitro-41-acetylamino-21-methoxyand ethoxy stilbene-2-sulphonic acids, 1:4-bis (21-sulpho-41-nitrostyryl)-benzene, 2-[41-nitro -21-sulphonic acid-styryl]-thiophene and -pyridine, 4-nitro-21-ethoxy- and 4-nitro-21-ethoxy-31 -methoxystilbene-2-sulphonic acids, 4-nitro-41-methyl -stilbene-2-sulphonic acid, 41-nitro-2141 -dimethylstilbene-2-sulphonic acid, 4-nitrostilbene-2-21-disulphonic acid and 4-nitro-41-dimethylaminostilbene-2-sulphonic acid. The products of the process may be employed as starting materials for the production of optical brightening agents. Specifications 668,200, 718,962 and 779,842 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH869372X | 1957-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB869372A true GB869372A (en) | 1961-05-31 |
Family
ID=4543903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13375/58A Expired GB869372A (en) | 1957-04-29 | 1958-04-28 | Improvements relating to 4-nitrostyryl-2-sulphonic acid compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB869372A (en) |
-
1958
- 1958-04-28 GB GB13375/58A patent/GB869372A/en not_active Expired
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