NO126860B - - Google Patents

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Info

Publication number: NO126860B
Authority: NO; Norway
Prior art keywords: ethyl; methoxy; acid; chlorobenzamido; benzenesulfinic
Prior art date: 1967-03-01

Application number

NO756/68A

Other languages

English (en)

Norwegian (no)

Inventor

R Weyer

K Muth

R Heerdt

H Weber

W Aumueller

Original Assignee

Hoechst Ag

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.)

1967-03-01

Filing date

1968-02-29

Publication date

1973-04-02

1968-02-29 Application filed by Hoechst Ag filed Critical Hoechst Ag

1973-04-02 Publication of NO126860B publication Critical patent/NO126860B/no

Links

238000000034 method Methods 0.000 claims description 9
150000001447 alkali salts Chemical class 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
150000003455 sulfinic acids Chemical class 0.000 claims description 3
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
239000000243 solution Substances 0.000 description 8
229920000137 polyphosphoric acid Polymers 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
-1 dioxane Chemical class 0.000 description 5
230000020477 pH reduction Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical class O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000460 chlorine Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
229960001330 hydroxycarbamide Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
APTFDFXACXBQDO-UHFFFAOYSA-N 1-butyl-3-hydroxyurea Chemical compound CCCCNC(=O)NO APTFDFXACXBQDO-UHFFFAOYSA-N 0.000 description 2
KDIAZPDILICRCD-UHFFFAOYSA-N 1-hydroxy-3-(4-methylcyclohexyl)urea Chemical compound CC1CCC(CC1)NC(=O)NO KDIAZPDILICRCD-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
QBJBUZKDFKCZMW-UHFFFAOYSA-N 1-cyclohexyl-3-hydroxyurea Chemical compound ONC(=O)NC1CCCCC1 QBJBUZKDFKCZMW-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SRNUYOADFVEOTP-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC=1C(=C(C=CC1)S(=O)O)CC Chemical compound C(C1=CC=CC=C1)(=O)NC=1C(=C(C=CC1)S(=O)O)CC SRNUYOADFVEOTP-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
XDGYHAAUHYNDMA-UHFFFAOYSA-N benzyl hypochlorite Chemical compound ClOCC1=CC=CC=C1 XDGYHAAUHYNDMA-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000007524 organic acids Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 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
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003672 ureas Chemical class 0.000 description 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
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- 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
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO756/68A 1967-03-01 1968-02-29 NO126860B (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF0051671		1967-03-01
DEF0051720		1967-03-04

Publications (1)

Publication Number	Publication Date
NO126860B true NO126860B (fr)	1973-04-02

Family

ID=25977590

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO756/68A NO126860B (fr)	1967-03-01	1968-02-29

Country Status (14)

Country	Link
AT (1)	AT276426B (fr)
CH (1)	CH532560A (fr)
DK (1)	DK127597B (fr)
ES (1)	ES350973A1 (fr)
FI (1)	FI49959C (fr)
IS (1)	IS844B6 (fr)
LU (1)	LU55566A1 (fr)
MC (1)	MC704A1 (fr)
NO (1)	NO126860B (fr)
OA (1)	OA02745A (fr)
PL (1)	PL79295B1 (fr)
SE (1)	SE342444B (fr)
SU (1)	SU451238A3 (fr)
YU (1)	YU33860B (fr)

1968
- 1968-02-09 FI FI680352A patent/FI49959C/fi active
- 1968-02-21 MC MC748A patent/MC704A1/fr unknown
- 1968-02-23 YU YU415/68A patent/YU33860B/xx unknown
- 1968-02-26 IS IS1729A patent/IS844B6/is unknown
- 1968-02-27 LU LU55566D patent/LU55566A1/xx unknown
- 1968-02-27 ES ES0350973A patent/ES350973A1/es not_active Expired
- 1968-02-27 CH CH279968A patent/CH532560A/de not_active IP Right Cessation
- 1968-02-27 DK DK77168AA patent/DK127597B/da not_active IP Right Cessation
- 1968-02-28 AT AT191368A patent/AT276426B/de active
- 1968-02-28 PL PL1968125522A patent/PL79295B1/pl unknown
- 1968-02-28 OA OA53187A patent/OA02745A/fr unknown
- 1968-02-29 SE SE2605/68A patent/SE342444B/xx unknown
- 1968-02-29 NO NO756/68A patent/NO126860B/no unknown
- 1968-03-01 SU SU1222722A patent/SU451238A3/ru active

Also Published As

Publication number	Publication date
ES350973A1 (es)	1969-12-01
FI49959C (fi)	1975-11-10
MC704A1 (fr)	1968-12-17
DK127597B (da)	1973-12-03
YU41568A (en)	1977-12-31
AT276426B (de)	1969-11-25
SE342444B (fr)	1972-02-07
SU451238A3 (ru)	1974-11-25
FI49959B (fr)	1975-07-31
PL79295B1 (en)	1975-06-30
LU55566A1 (fr)	1969-10-01
CH532560A (de)	1973-01-15
OA02745A (fr)	1970-12-15
IS844B6 (is)	1974-01-15
IS1729A7 (is)	1968-09-02
YU33860B (en)	1978-06-30

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US2519886A (en)	1950-08-22	Beta-bimethylaminoethylphenothia
US3406199A (en)	1968-10-15	Benzenesulfonyl ureas and process for their manufacture
NO126860B (fr)	1973-04-02
NO159998B (no)	1988-11-21	Analogifremgangsmaate ved fremstilling av et nytt terapeutisk aktivtsulfonamidderivat.
NO171182B (no)	1992-10-26	Vandig geldannende blanding egnet for selektiv permeabilitetsmodifikasjon av underjordiske lag ved hydrokarbonutvinning
NO814468L (no)	1982-07-01	Tiazolinderivater, fremgangsmaate til deres fremstilling, deres anvendelse samt farmasoeytiske preparater paa basis av disse forbindelser
NO122920B (fr)	1971-09-06
KR880002706B1 (ko)	1988-12-26	설포닐 우레아의 제조방법
Kharasch et al.	1954	Derivatives of sulfenic acids. XV. A new synthesis of thiophenols
Ogata et al.	1951	The Chemistry of 1-Naphthaleneacetic Acid Derivatives
NO803612L (no)	1981-06-02	Benzensulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser samt deres anvendelse
US5719294A (en)	1998-02-17	Process for preparing N-cyclohexylthiophthalimide
US3925557A (en)	1975-12-09	Anti-allergic pharmaceutical compositions
US3998841A (en)	1976-12-21	Chlorothio-n-phthalimide and process therefor
NO117175B (fr)	1969-07-14
CH638798A5 (de)	1983-10-14	5-sulfamoyl-orthanilsaeuren und verfahren zu ihrer herstellung.
DE2828079A1 (de)	1980-01-10	Sulfonylharnstoffe und verfahren zu ihrer herstellung
US4076729A (en)	1978-02-28	(4-Oxo-4H-1-benzopyran-3-yl)aminooxoacetic acids and their derivatives
US3850950A (en)	1974-11-26	Benzenesulfonyl ureas and process for their manufacture
PEARL	1945	SULFANILAMIDES FROM p-AZOBENZENESULFONYL CHLORIDE1
NO132094B (fr)	1975-06-09
NO123429B (fr)	1971-11-15
PT1005462E (pt)	2007-01-31	Processo para o fabrico de 2, 2-dioxido de 3-isopropil-1h-2,1,3-benzotiadiazin-4 (3h)-ona