NO133893B - - Google Patents

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Info

Publication number: NO133893B
Authority: NO; Norway
Prior art keywords: pyridyl; methane; bis; hydroxyphenyl; ester
Prior art date: 1969-01-29

Application number

NO30770A

Other languages

English (en)

Norwegian (no)

Other versions

NO133893C (de

Inventor

E Seeger

H Machleidt

Original Assignee

Thomae Gmbh Dr K

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.)

1969-01-29

Filing date

1970-01-28

Publication date

1976-04-05

1970-01-28 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1976-04-05 Publication of NO133893B publication Critical patent/NO133893B/no

1976-07-14 Publication of NO133893C publication Critical patent/NO133893C/no

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 9
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
239000003513 alkali Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
150000004292 cyclic ethers Chemical group 0.000 claims description 3
150000007530 organic bases Chemical group 0.000 claims description 3
229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000002036 chloroform fraction Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
HGBGABMSTHQFNJ-UHFFFAOYSA-N 1,4-dioxane;sulfur trioxide Chemical compound O=S(=O)=O.C1COCCO1 HGBGABMSTHQFNJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000007017 scission Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 description 1
HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
QKCXECLVPQOFSK-UHFFFAOYSA-N S(=O)(=O)=O.C(C)N1CCOCC1 Chemical compound S(=O)(=O)=O.C(C)N1CCOCC1 QKCXECLVPQOFSK-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
-1 sulfuric acid ester Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)

NO30770A 1969-01-29 1970-01-28 NO133893C (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19691904322 DE1904322A1 (de)	1969-01-29	1969-01-29	Verfahren zur Herstellung des Dischwefelsaeurehalbesters des Bis-(4-hydroxyphenyl)-(pyridyl-2)-methans und dessen Salze

Publications (2)

Publication Number	Publication Date
NO133893B true NO133893B (de)	1976-04-05
NO133893C NO133893C (de)	1976-07-14

Family

ID=5723688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO30770A NO133893C (de)	1969-01-29	1970-01-28

Country Status (9)

Country	Link
AT (1)	AT292703B (de)
BR (1)	BR7016449D0 (de)
CH (1)	CH515902A (de)
DE (1)	DE1904322A1 (de)
DK (1)	DK133671B (de)
ES (1)	ES375976A1 (de)
FI (1)	FI52340C (de)
NO (1)	NO133893C (de)
SE (1)	SE366982B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6288328B1 (en)	1999-03-19	2001-09-11	Avaya Technology Corp.	Coaxial cable having effective insulated conductor rotation

1969
- 1969-01-29 DE DE19691904322 patent/DE1904322A1/de active Pending
1970
- 1970-01-19 FI FI13770A patent/FI52340C/fi active
- 1970-01-27 CH CH115070A patent/CH515902A/de not_active IP Right Cessation
- 1970-01-28 DK DK41070A patent/DK133671B/da unknown
- 1970-01-28 NO NO30770A patent/NO133893C/no unknown
- 1970-01-28 ES ES375976A patent/ES375976A1/es not_active Expired
- 1970-01-29 BR BR21644970A patent/BR7016449D0/pt unknown
- 1970-01-29 SE SE117670A patent/SE366982B/xx unknown
- 1970-01-29 AT AT84170A patent/AT292703B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE366982B (de)	1974-05-13
DE1904322A1 (de)	1970-08-06
FI52340C (fi)	1977-08-10
BR7016449D0 (pt)	1973-04-05
CH515902A (de)	1971-11-30
AT292703B (de)	1971-09-10
ES375976A1 (es)	1972-10-16
FI52340B (de)	1977-05-02
DK133671B (da)	1976-06-28
NO133893C (de)	1976-07-14
DK133671C (de)	1976-11-15

Publication	Publication Date	Title
SU613724A3 (ru)	1978-06-30	Способ получени 8-тиометил-эрголинов или их солей
NO140069B (no)	1979-03-19	Pulverformet, lagringsbestandig vaskemiddelblanding
US2018792A (en)	1935-10-29	Process for the manufacture of hydroxypyrene
EP3422855B1 (de)	2020-07-08	Verfahren zur herstellung von 4-alkoxy-3-hydroxypicolinsäuren
NO133893B (de)	1976-04-05
US4115652A (en)	1978-09-19	Process for the preparation of amino-nitrophenols
NO115944B (de)	1968-12-30
NO791772L (no)	1979-12-03	Polyjodbenzen-roentgenkontrastmidler.
US2050958A (en)	1936-08-11	3-hydroxydiphenyleneoxide-2-carboxylic acid
US3471506A (en)	1969-10-07	Process for preparing 5-chloro-2,3-pyridine diol
NO144795B (no)	1981-08-03	Fremgangsmaate ved fremstilling av n1-(2-tetrahydrofuryl)-5-fluoruracil
SU383373A1 (ru)	1975-05-05	Способ получени динатриевой соли дисульфида 3,3-дипропандисульфокислоты
US6133447A (en)	2000-10-17	Process for the preparation of substituted pyridines
NO149027B (no)	1983-10-24	Innretning til aa paafoere et belegg paa en neddykket overflate
SU561504A3 (ru)	1977-06-05	Способ получени 2,2",3,3"тетракарбоксидиангидрида дифенилового эфира
SU532340A3 (ru)	1976-10-15	Способ получени 3-(5нитро-1-метил2-имидазолил)- -триазоло(4,3-в) пиридазинов или их солей
US2097726A (en)	1937-11-02	Process for the manufacture of sulphonic acids from aryl ethylenes and the products thereof
SE439012B (sv)	1985-05-28	Forfarande for framstellning av 5-sulfamoyl-ortanilsyror
US3654292A (en)	1972-04-04	Manufacture of 3 5-dichloro-2 6-difluoro - 4 - hydroxypyridine and salts thereof
KR0129550B1 (ko)	1998-04-09	아미노카르보닐 치환 피리딘술핀산 또는 그의 염
US1069296A (en)	1913-08-05	Derivatives of phenylcinchoninic acid.
US1979033A (en)	1934-10-30	Process for the manufacture of nsulphoethyl compounds of arylamino sulphonic acids
KR950012536B1 (ko)	1995-10-18	2-니트로-4-설파밀디페닐아민 염료의 제조방법
US2648689A (en)	1953-08-11	Preparation of p' (benzoylsulfamyl) phthalanilic acid
US1973001A (en)	1934-09-11	Amino-anthraquinone sulpho-chlorides and a process of preparing them