IL24192A - 1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation - Google Patents

1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation

Info

Publication number: IL24192A
Authority: IL; Israel
Prior art keywords: tolylsulfonyl; amino; group; member selected; chloro
Prior art date: 1964-09-15

Application number

IL24192A

Other languages

English (en)

Original Assignee

Upjohn Co

Priority date (The priority date 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 date listed.)

1964-09-15

Filing date

1965-08-18

Publication date

1969-03-27

1965-08-18 Application filed by Upjohn Co filed Critical Upjohn Co

1969-03-27 Publication of IL24192A publication Critical patent/IL24192A/en

Links

238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title description 20
BPTIOJPNCPTPDO-UHFFFAOYSA-N 3-(benzenesulfonyl)-1h-benzimidazol-2-one Chemical class O=C1NC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 BPTIOJPNCPTPDO-UHFFFAOYSA-N 0.000 title description 2
KAMUXRFLMIRMEZ-UHFFFAOYSA-N 3-(benzenesulfonyl)-1h-benzimidazole-2-thione Chemical class C12=CC=CC=C2NC(=S)N1S(=O)(=O)C1=CC=CC=C1 KAMUXRFLMIRMEZ-UHFFFAOYSA-N 0.000 title description 2
-1 lower-alkyl Chemical class 0.000 claims description 69
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 27
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
KGFXBBKICOQXTC-UHFFFAOYSA-N n-(2-aminophenyl)benzenesulfonamide Chemical compound NC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 KGFXBBKICOQXTC-UHFFFAOYSA-N 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
AQUNQTJQZYZXMR-UHFFFAOYSA-N n-(2-aminophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1N AQUNQTJQZYZXMR-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
BGONMSRDLPYCGO-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-1h-benzimidazole-2-thione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=S)NC2=CC=CC=C21 BGONMSRDLPYCGO-UHFFFAOYSA-N 0.000 claims description 2
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 claims 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000012065 filter cake Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
239000012431 aqueous reaction media Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
QZUVZJYESQWXSW-UHFFFAOYSA-N n-(2-amino-4-methylphenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C)C=C1N QZUVZJYESQWXSW-UHFFFAOYSA-N 0.000 description 3
ONFVSYRDKYBUAR-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1[N+]([O-])=O ONFVSYRDKYBUAR-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
VOTXWUCYIOPNNR-UHFFFAOYSA-N 2-chloro-6-nitroaniline Chemical compound NC1=C(Cl)C=CC=C1[N+]([O-])=O VOTXWUCYIOPNNR-UHFFFAOYSA-N 0.000 description 2
PNIZZXSAQQVBRY-UHFFFAOYSA-N 4-methyl-n-(4-methyl-2-nitrophenyl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C)C=C1[N+]([O-])=O PNIZZXSAQQVBRY-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QFDQMLXLNKXRON-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)NC1=C(C=C(C(=C1)Cl)Cl)N)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)NC1=C(C=C(C(=C1)Cl)Cl)N)C QFDQMLXLNKXRON-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
XARDPQJTCVUKGC-UHFFFAOYSA-N 2-iodo-6-nitroaniline Chemical compound NC1=C(I)C=CC=C1[N+]([O-])=O XARDPQJTCVUKGC-UHFFFAOYSA-N 0.000 description 1
ZUSYPWKBRJWZIA-UHFFFAOYSA-N 2-nitro-5-propoxyaniline Chemical group CCCOC1=CC=C([N+]([O-])=O)C(N)=C1 ZUSYPWKBRJWZIA-UHFFFAOYSA-N 0.000 description 1
XKPIZUOWBPXNLD-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-1h-benzimidazol-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)NC2=CC=CC=C21 XKPIZUOWBPXNLD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
FOPBPYCNUNCYAU-UHFFFAOYSA-N 4-bromo-n-(4-methyl-2-nitrophenyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 FOPBPYCNUNCYAU-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical group ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
RUQAPQLDPWSAQM-UHFFFAOYSA-N 4-ethyl-2-nitroaniline Chemical group CCC1=CC=C(N)C([N+]([O-])=O)=C1 RUQAPQLDPWSAQM-UHFFFAOYSA-N 0.000 description 1
AEEARKNYRMBNSW-UHFFFAOYSA-N 4-methyl-n-(2-nitrophenyl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1[N+]([O-])=O AEEARKNYRMBNSW-UHFFFAOYSA-N 0.000 description 1
SXKXVEBWNNCSSE-UHFFFAOYSA-N 5-tert-butyl-2-nitroaniline Chemical compound CC(C)(C)C1=CC=C([N+]([O-])=O)C(N)=C1 SXKXVEBWNNCSSE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241001061127 Thione Species 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
230000035619 diuresis Effects 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
NNIQFHPICOVQFS-UHFFFAOYSA-N n-(2-amino-4-methylphenyl)benzenesulfonamide Chemical group NC1=CC(C)=CC=C1NS(=O)(=O)C1=CC=CC=C1 NNIQFHPICOVQFS-UHFFFAOYSA-N 0.000 description 1
QYEQJQLZLZRQEB-UHFFFAOYSA-N n-(2-nitrophenyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 QYEQJQLZLZRQEB-UHFFFAOYSA-N 0.000 description 1
IZUQZLGWRCYWCB-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]aniline Chemical compound C1=CC(OC)=CC=C1C=NNC1=CC=CC=C1 IZUQZLGWRCYWCB-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL24192A 1964-09-15 1965-08-18 1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation IL24192A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US396722A US3405136A (en)	1964-09-15	1964-09-15	1-phenylsulfonyl-2-benzimidazo-linones and 1-phenylsulfonyl-2-benzimidazolinethiones

Publications (1)

Publication Number	Publication Date
IL24192A true IL24192A (en)	1969-03-27

Family

ID=23568389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL24192A IL24192A (en)	1964-09-15	1965-08-18	1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation

Country Status (5)

Country	Link
US (1)	US3405136A (de)
CH (1)	CH454156A (de)
GB (1)	GB1118131A (de)
IL (1)	IL24192A (de)
NL (1)	NL6512029A (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3895025A (en) *	1973-03-29	1975-07-15	Du Pont	2-Benzimidazolethiol preparation
US4118573A (en) *	1975-11-24	1978-10-03	Eli Lilly And Company	Substituted 1-sulfonylbenzimidazoles
CH640548A5 (de) *	1979-08-28	1984-01-13	Ciba Geigy Ag	Flammwidrige kunststofformmasse.
JPS58118558A (ja) *	1982-01-05	1983-07-14	Mitsui Toatsu Chem Inc	３−ニトロ−４−メチルベンゼンスルホン−２−クロル−４−ニトロアニライドと農園芸用殺菌剤
FR2708608B1 (fr) *	1993-07-30	1995-10-27	Sanofi Sa	Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3235559A (en) *		1966-02-15		Process for the production of z-mercaptobenzimidazole
US2927116A (en) *		1960-03-01		Chlorobenzimidazolone compounds
DE557138C (de) *	1931-01-01	1932-08-19	Ig Farbenindustrie Ag	Alterungsschutzmittel fuer natuerlichen und synthetischen Kautschuk
US2701249A (en) *	1951-01-30	1955-02-01	Merck & Co Inc	Preparation of 2-mercapto-5, 6-dimethylbenzimidazole and 5, 6-dimethylbenzimidazole
US2642396A (en) *	1952-05-01	1953-06-16	Texas Co	Hydrocarbon oil containing a mercaptobenzimidazole
US2933503A (en) *	1957-01-14	1960-04-19	Merck & Co Inc	Benzimidazole derivatives
US3056777A (en) *	1960-12-19	1962-10-02	Merck & Co Inc	New benzimidazoles
BE627013A (de) *	1962-01-11
US3246035A (en) *	1962-11-28	1966-04-12	Fmc Corp	Preparation of non-vicinal aromatic diamines

1964
- 1964-09-15 US US396722A patent/US3405136A/en not_active Expired - Lifetime
1965
- 1965-08-11 GB GB34400/65A patent/GB1118131A/en not_active Expired
- 1965-08-18 IL IL24192A patent/IL24192A/en unknown
- 1965-09-07 CH CH1245265A patent/CH454156A/de unknown
- 1965-09-15 NL NL6512029A patent/NL6512029A/xx unknown

Also Published As

Publication number	Publication date
GB1118131A (en)	1968-06-26
US3405136A (en)	1968-10-08
NL6512029A (de)	1966-03-16
CH454156A (de)	1968-04-15

Publication	Publication Date	Title
Smith et al.	1951	The Synthesis of Heterocyclic Compounds from Aryl Azides. I. Bromo and Nitro Carbazoles1
SU691089A3 (ru)	1979-10-05	Способ получени карбонилзамещенных 1-сульфонилбензимидазолов
Adams et al.	1950	Quinone imides. I. p-Quinone disulfonimides
US3480642A (en)	1969-11-25	Process for producing 2-carbalkoxyaminobenzimidazoles
US2965655A (en)	1960-12-20	Process for preparing substituted 1-amino 2, 4-benzene-disulfonamides
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