BE456915A - - Google Patents

Info

Publication number: BE456915A
Authority: BE; Belgium
Prior art keywords: acids; esters; halogen; ammonia; sulfocarbonimides
Prior art date: 1943-08-12

Application number

BE456915A

Other languages

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.)

1943-08-12

Filing date

1944-07-22

Publication date

1944-08-31

1944-07-22 Application filed filed Critical

1944-08-31 Publication of BE456915A publication Critical patent/BE456915A/fr

Links

QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
-1 aliphatic alcohols Chemical class 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
238000003756 stirring Methods 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
239000007864 aqueous solution 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
239000004202 carbamide Substances 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
BAQGCWNPCFABAY-UHFFFAOYSA-N methyl 2-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S BAQGCWNPCFABAY-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
229940103494 thiosalicylic acid Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)

BE456915A 1943-08-12 1944-07-22 BE456915A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE456915X		1943-08-12

Publications (1)

Publication Number	Publication Date
BE456915A true BE456915A (de)	1944-08-31

Family

ID=110471

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
BE456915A BE456915A (de)	1943-08-12	1944-07-22
BE457543A BE457543R (de)	1943-08-12	1944-09-13

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
BE457543A BE457543R (de)	1943-08-12	1944-09-13

Country Status (1)

Country	Link
BE (2)	BE456915A (de)

1944
- 1944-07-22 BE BE456915A patent/BE456915A/fr unknown
- 1944-09-13 BE BE457543A patent/BE457543R/fr active

Also Published As

Publication number	Publication date
BE457543R (de)	1944-10-31

Publication	Publication Date	Title
EP0055951B1 (de)	1984-05-30	Verfahren zur Herstellung von Anthrachinon und dessen substituierten Derivaten
EP0008548A1 (de)	1980-03-05	Verfahren zur Herstellung von Benzothiazol-Disulfid
BE456915A (de)	1944-08-31
EP0149407A2 (de)	1985-07-24	Verfahren zur Herstellung von Brombenzaldehyden-Hydroxy und/oder Alkoxy substituiert
FR2468585A1 (fr)	1981-05-08	Procede de preparation de la 1,4-diamino-2,3-dicyanoanthraquinone
EP0025620B1 (de)	1983-06-22	Verfahren zur Herstellung substituierter Anthrachinone
BE553871A (de)
FR2510102A1 (fr)	1983-01-28	Procede de purification de derives d'acides phenoxybenzoiques
FR2486527A1 (fr)	1982-01-15	Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide
US5250741A (en)	1993-10-05	Process for the preparation of 5-alkoxy-2-nitroso phenols
Clarke et al.	1924	A modification of the sandmeyer synthesis of nitriles
EP0292362B1 (de)	1992-08-26	Verfahren zur Herstellung von halogenierten Imiden
EP0349382B1 (de)	1992-10-14	Verfahren zur Reinigung von Dihydroxybiphenylen
FR2543948A1 (fr)	1984-10-12	Procede de preparation de l'acide 1-naphtol-4-sulfonique
BE846038A (fr)	1976-12-31	Acides anthraquinone-disulfoniques mixtes
FR2470109A1 (fr)	1981-05-29	Procede de preparation d'acides meta-hydroxybenzoiques
EP0185569A1 (de)	1986-06-25	Verfahren zur Herstellung von Anthrachinon-Küpenfarbstoffen, durch dieses Verfahren erhaltene Farbstoffe und die mit diesen Farbstoffen gefärbten Textilmaterialien
FR2510105A1 (fr)	1983-01-28	Procede de preparation d'acides phenoxybenzoiques
BE442010A (de)
CH658860A5 (fr)	1986-12-15	Procede de preparation d'acides aryloxybenzoiques a groupe sulfonamide.
BE442195A (de)
CH669380A5 (de)	1989-03-15
BE555169A (de)
CH108490A (fr)	1925-01-16	Procédé de préparation de la phénylrosinduline.
JPH0393737A (ja)	1991-04-18	４，４’‐ジヒドロキシビフェニルの製造方法