DD150896A5 - Verfahren zur herstellung von n-dialkylaminomethyl-s,s-diarylsulfoximiden - Google Patents

Verfahren zur herstellung von n-dialkylaminomethyl-s,s-diarylsulfoximiden Download PDF

Info

Publication number: DD150896A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; preparation; water; heterocyclic ring; optionally substituted
Prior art date: 1979-05-23

Application number

DD80221317A

Other languages

German (de)

English (en)

Inventor

Manfred Haake

Theodorus Setijadi

Kurt-Henning Ahrens

Original Assignee

Heumann Ludwig & Co Gmbh

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.)

1979-05-23

Filing date

1980-05-22

Publication date

1981-09-23

1980-05-22 Application filed by Heumann Ludwig & Co Gmbh filed Critical Heumann Ludwig & Co Gmbh

1981-09-23 Publication of DD150896A5 publication Critical patent/DD150896A5/de

Links

229910052717 sulfur Inorganic materials 0.000 title claims abstract description 44
238000002360 preparation method Methods 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title claims abstract description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 27
239000002904 solvent Substances 0.000 claims abstract description 18
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
150000003839 salts Chemical group 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
238000006683 Mannich reaction Methods 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000000047 product Substances 0.000 description 8
239000003921 oil Substances 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000008098 formaldehyde solution Substances 0.000 description 6
-1 alkali metal salt Chemical class 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
229940102396 methyl bromide Drugs 0.000 description 4
ZKJJBMKFLUOHAP-UHFFFAOYSA-N morpholin-4-ylmethylimino-oxo-diphenyl-lambda6-sulfane Chemical compound O1CCN(CC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 ZKJJBMKFLUOHAP-UHFFFAOYSA-N 0.000 description 4
238000010792 warming Methods 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000003958 fumigation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
XQGOFKFATFKSFH-UHFFFAOYSA-N N-ethyl-N-[[[oxo(diphenyl)-lambda6-sulfanylidene]amino]methyl]ethanamine Chemical compound C(C)N(CC)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 XQGOFKFATFKSFH-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000007975 iminium salts Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
YRBWBVBBWHYPJE-UHFFFAOYSA-N oxo-diphenyl-(piperidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 YRBWBVBBWHYPJE-UHFFFAOYSA-N 0.000 description 2
MSWZGWJZZCNBPR-UHFFFAOYSA-N oxo-diphenyl-(pyrrolidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 MSWZGWJZZCNBPR-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
230000002048 spasmolytic effect Effects 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000005555 sulfoximide group Chemical group 0.000 description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
MIFZZKZNMWTHJK-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)morpholine Chemical compound C1COCCN1CN1CCOCC1 MIFZZKZNMWTHJK-UHFFFAOYSA-N 0.000 description 1
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
FYEFFJPBPRIIEY-UHFFFAOYSA-N BrC1=CC=C(C=C1)S(=O)=N Chemical compound BrC1=CC=C(C=C1)S(=O)=N FYEFFJPBPRIIEY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002309 gasification Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KNPJTNDEHOFWKA-UHFFFAOYSA-N imino-oxo-diphenyl-$l^{6}-sulfane Chemical compound C=1C=CC=CC=1S(=O)(=N)C1=CC=CC=C1 KNPJTNDEHOFWKA-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
NDMMNVRSMCKNEO-UHFFFAOYSA-N n,n-dimethyl-1-[[oxo(diphenyl)-$l^{6}-sulfanylidene]amino]methanamine Chemical compound C=1C=CC=CC=1S(=O)(=NCN(C)C)C1=CC=CC=C1 NDMMNVRSMCKNEO-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000010490 three component reaction Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

DD80221317A 1979-05-23 1980-05-22 Verfahren zur herstellung von n-dialkylaminomethyl-s,s-diarylsulfoximiden DD150896A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2920958A DE2920958C2 (de)	1979-05-23	1979-05-23	Verfahren zur Herstellung von S,S-Diarylsulfoximidderivaten

Publications (1)

Publication Number	Publication Date
DD150896A5 true DD150896A5 (de)	1981-09-23

Family

ID=6071557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221317A DD150896A5 (de)	1979-05-23	1980-05-22	Verfahren zur herstellung von n-dialkylaminomethyl-s,s-diarylsulfoximiden

Country Status (9)

Country	Link
JP (1)	JPS5625151A (it)
AR (1)	AR225039A1 (it)
AT (1)	AT371805B (it)
DD (1)	DD150896A5 (it)
DE (1)	DE2920958C2 (it)
ES (1)	ES491696A0 (it)
HU (1)	HU180140B (it)
IT (1)	IT1140964B (it)
PT (1)	PT71284A (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9000303D0 (en) *	1990-01-06	1990-03-07	Pfizer Ltd	Therapeutic agents

1979
- 1979-05-23 DE DE2920958A patent/DE2920958C2/de not_active Expired
1980
- 1980-05-05 AT AT0237880A patent/AT371805B/de not_active IP Right Cessation
- 1980-05-20 AR AR281124A patent/AR225039A1/es active
- 1980-05-20 IT IT22192/80A patent/IT1140964B/it active
- 1980-05-21 HU HU801273A patent/HU180140B/hu unknown
- 1980-05-21 ES ES491696A patent/ES491696A0/es active Granted
- 1980-05-21 JP JP6838880A patent/JPS5625151A/ja active Pending
- 1980-05-21 PT PT71284A patent/PT71284A/pt unknown
- 1980-05-22 DD DD80221317A patent/DD150896A5/de unknown

Also Published As

Publication number	Publication date
ES8102111A1 (es)	1981-01-16
IT8022192A0 (it)	1980-05-20
AT371805B (de)	1983-08-10
ATA237880A (de)	1982-12-15
AR225039A1 (es)	1982-02-15
PT71284A (de)	1980-06-01
JPS5625151A (en)	1981-03-10
ES491696A0 (es)	1981-01-16
DE2920958B1 (de)	1980-09-18
HU180140B (en)	1983-02-28
IT1140964B (it)	1986-10-10
DE2920958C2 (de)	1981-06-11

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