JPS59135255A - フルオラン化合物 - Google Patents
フルオラン化合物Info
- Publication number
- JPS59135255A JPS59135255A JP58008095A JP809583A JPS59135255A JP S59135255 A JPS59135255 A JP S59135255A JP 58008095 A JP58008095 A JP 58008095A JP 809583 A JP809583 A JP 809583A JP S59135255 A JPS59135255 A JP S59135255A
- Authority
- JP
- Japan
- Prior art keywords
- color
- toluene
- general formula
- fluorane
- compound
- 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.)
- Granted
Links
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 title description 5
- -1 cyclic alkyl Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
- 150000001875 compounds Chemical class 0.000 description 29
- 239000000047 product Substances 0.000 description 28
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 27
- 229940035422 diphenylamine Drugs 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 239000012965 benzophenone Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- FQNKTJPBXAZUGC-UHFFFAOYSA-N 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FQNKTJPBXAZUGC-UHFFFAOYSA-N 0.000 description 6
- QPNFUBAIQZJEPO-UHFFFAOYSA-N 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPNFUBAIQZJEPO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical class FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011268 mixed slurry Substances 0.000 description 2
- KVFWVDXRQNGMEV-UHFFFAOYSA-N n-fluorobutan-1-amine Chemical compound CCCCNF KVFWVDXRQNGMEV-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OHLGNIVLMQBOLM-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-methylpiperidine Chemical compound C1C(C)CCCN1S(=O)(=O)C1=CC=C(Br)C=C1 OHLGNIVLMQBOLM-UHFFFAOYSA-N 0.000 description 1
- CBNDEXDYZUNXBF-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-methylpiperazine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(Br)C=C1 CBNDEXDYZUNXBF-UHFFFAOYSA-N 0.000 description 1
- GTXWMYDMGGSQOD-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-methylpiperidine Chemical compound C1CC(C)CCN1S(=O)(=O)C1=CC=C(Br)C=C1 GTXWMYDMGGSQOD-UHFFFAOYSA-N 0.000 description 1
- JMOJWOSNSJXQMT-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonylpyrrolidine Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCCC1 JMOJWOSNSJXQMT-UHFFFAOYSA-N 0.000 description 1
- FXKRATLJGPAUHB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CCCC1 FXKRATLJGPAUHB-UHFFFAOYSA-N 0.000 description 1
- JWJRLABLXQZFAR-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonylmorpholine Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1CCOCC1 JWJRLABLXQZFAR-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- DUDXQHGWYWTEGF-UHFFFAOYSA-N N-phenyl-6-sulfonylcyclohexa-2,4-dien-1-amine Chemical compound S(=O)(=O)=C1C(NC2=CC=CC=C2)C=CC=C1 DUDXQHGWYWTEGF-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- DHTSROUAFKMQSJ-UHFFFAOYSA-N n-butyl-n-fluorobutan-1-amine Chemical compound CCCCN(F)CCCC DHTSROUAFKMQSJ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58008095A JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58008095A JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59135255A true JPS59135255A (ja) | 1984-08-03 |
| JPH0435505B2 JPH0435505B2 (enrdf_load_stackoverflow) | 1992-06-11 |
Family
ID=11683749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58008095A Granted JPS59135255A (ja) | 1983-01-22 | 1983-01-22 | フルオラン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59135255A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9422235B2 (en) | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
-
1983
- 1983-01-22 JP JP58008095A patent/JPS59135255A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9422235B2 (en) | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0435505B2 (enrdf_load_stackoverflow) | 1992-06-11 |
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