GB1586366A - Process for the preparation of 4,9-dihydronaphtho(2,3-b)thiophene-4,9-diones - Google Patents
Process for the preparation of 4,9-dihydronaphtho(2,3-b)thiophene-4,9-diones Download PDFInfo
- Publication number
- GB1586366A GB1586366A GB11354/77A GB1135477A GB1586366A GB 1586366 A GB1586366 A GB 1586366A GB 11354/77 A GB11354/77 A GB 11354/77A GB 1135477 A GB1135477 A GB 1135477A GB 1586366 A GB1586366 A GB 1586366A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiophene
- dihydronaphtho
- mixture
- ring
- formylmethylthio
- 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
- 238000000034 method Methods 0.000 title claims description 34
- GDUFLCCHLCZVCJ-UHFFFAOYSA-N benzo[f][1]benzothiole-4,9-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1SC=C2 GDUFLCCHLCZVCJ-UHFFFAOYSA-N 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 20
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 14
- -1 8-amino-5,7-dibromo-4,9 dihydronaphtho[2,3-b]thiophene-4,9-dione Chemical compound 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 235000011054 acetic acid Nutrition 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229920002994 synthetic fiber Polymers 0.000 claims description 7
- 239000004758 synthetic textile Substances 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 6
- QJFUMFCCMJJLIE-UHFFFAOYSA-N ethanethial Chemical class CC=S QJFUMFCCMJJLIE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000012505 colouration Methods 0.000 claims description 5
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000007639 printing Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000000191 1,4-naphthoquinones Chemical class 0.000 claims description 2
- VICVLCKDMXAERS-UHFFFAOYSA-N 5,8-dihydroxybenzo[f][1]benzothiole-4,9-dione Chemical compound O=C1C=2C(O)=CC=C(O)C=2C(=O)C2=C1C=CS2 VICVLCKDMXAERS-UHFFFAOYSA-N 0.000 claims description 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- CYKIHIBNSFRKQP-UHFFFAOYSA-N benzo[f][1]benzothiole Chemical class C1=CC=C2C=C(SC=C3)C3=CC2=C1 CYKIHIBNSFRKQP-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims description 2
- 238000010023 transfer printing Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- UIGMKTNIMNGVBZ-UHFFFAOYSA-N 2-(4-oxo-1-sulfanylidenenaphthalen-2-yl)acetaldehyde Chemical compound C(=O)CC=1C(C2=CC=CC=C2C(C1)=O)=S UIGMKTNIMNGVBZ-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 101000743114 Homo sapiens WASH complex subunit 4 Proteins 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- MPLKAMKBGNHILL-UHFFFAOYSA-N O=C1C=2C(N)=CC=CC=2C(=O)C2=C1SC=C2 Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1SC=C2 MPLKAMKBGNHILL-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 102100038143 WASH complex subunit 4 Human genes 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- LCECTYUHGUTJLE-UHFFFAOYSA-N n-(5,8-dioxonaphthalen-1-yl)acetamide Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2NC(=O)C LCECTYUHGUTJLE-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/74—Naphthothiophenes
-
- 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
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11354/77A GB1586366A (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of 4,9-dihydronaphtho(2,3-b)thiophene-4,9-diones |
| DE19782808321 DE2808321A1 (de) | 1977-03-17 | 1978-02-27 | Verfahren zur herstellung von 4,9- dihydronaphtho eckige klammer auf ,3-b eckige klammer zu -thiophen-4,9-dionen |
| JP2196678A JPS53119864A (en) | 1977-03-17 | 1978-02-27 | Process for preparing 4*99dihydronaphto*2*33b*thiophenee 4*99dion |
| IT21250/78A IT1158664B (it) | 1977-03-17 | 1978-03-15 | Procedimento per la preparazione di certi 4,9-diidro-nafto (2,3-b) tiofen-4,9-dioni,noti anche come tiofantrachinoni |
| FR7807635A FR2383940A1 (fr) | 1977-03-17 | 1978-03-16 | Procede de production de 4,9-dihydronaphto-(2,3-b)- thiophene-4,9-diones, produits obtenus et leurs applications tinctoriales |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11354/77A GB1586366A (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of 4,9-dihydronaphtho(2,3-b)thiophene-4,9-diones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1586366A true GB1586366A (en) | 1981-03-18 |
Family
ID=9984717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11354/77A Expired GB1586366A (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of 4,9-dihydronaphtho(2,3-b)thiophene-4,9-diones |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS53119864A (it) |
| DE (1) | DE2808321A1 (it) |
| FR (1) | FR2383940A1 (it) |
| GB (1) | GB1586366A (it) |
| IT (1) | IT1158664B (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW252136B (it) * | 1992-10-08 | 1995-07-21 | Ciba Geigy |
-
1977
- 1977-03-17 GB GB11354/77A patent/GB1586366A/en not_active Expired
-
1978
- 1978-02-27 JP JP2196678A patent/JPS53119864A/ja active Pending
- 1978-02-27 DE DE19782808321 patent/DE2808321A1/de active Pending
- 1978-03-15 IT IT21250/78A patent/IT1158664B/it active
- 1978-03-16 FR FR7807635A patent/FR2383940A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2808321A1 (de) | 1978-09-21 |
| JPS53119864A (en) | 1978-10-19 |
| IT1158664B (it) | 1987-02-25 |
| FR2383940A1 (fr) | 1978-10-13 |
| IT7821250A0 (it) | 1978-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |