NO123929B - - Google Patents
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- Publication number
- NO123929B NO123929B NO478868A NO478868A NO123929B NO 123929 B NO123929 B NO 123929B NO 478868 A NO478868 A NO 478868A NO 478868 A NO478868 A NO 478868A NO 123929 B NO123929 B NO 123929B
- Authority
- NO
- Norway
- Prior art keywords
- iodide
- bromide
- methyl
- dimethyl
- reacted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012022 methylating agents Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- RUHVDRGWCIAFLG-UHFFFAOYSA-N n,n-dimethyl-2-phenoxyethanamine Chemical compound CN(C)CCOC1=CC=CC=C1 RUHVDRGWCIAFLG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MROWHKRJXTVSGQ-UHFFFAOYSA-N n-(2-phenoxyethyl)-2-phenylethanamine Chemical compound C=1C=CC=CC=1CCNCCOC1=CC=CC=C1 MROWHKRJXTVSGQ-UHFFFAOYSA-N 0.000 claims 1
- XTNXLNGNJZRBRW-UHFFFAOYSA-N n-benzyl-2-phenoxyethanamine Chemical compound C=1C=CC=CC=1CNCCOC1=CC=CC=C1 XTNXLNGNJZRBRW-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 3
- -1 1-o-methylbenzylamino-2-phenoxyethane Chemical compound 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229940107816 ammonium iodide Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- ABXRTJHEVCZIAG-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-methylbenzene Chemical compound CC1=CC=CC=C1OCCBr ABXRTJHEVCZIAG-UHFFFAOYSA-N 0.000 description 2
- PURSZYWBIQIANP-UHFFFAOYSA-N 1-(bromomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CBr PURSZYWBIQIANP-UHFFFAOYSA-N 0.000 description 2
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- MAAOCTAUJRPCTL-UHFFFAOYSA-N n,n-dimethyl-2-(2-methylphenoxy)ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C MAAOCTAUJRPCTL-UHFFFAOYSA-N 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ZDEJJQHQIOWTPC-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1OCCBr ZDEJJQHQIOWTPC-UHFFFAOYSA-N 0.000 description 1
- AHOFWSHLRKOJBS-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OCCBr AHOFWSHLRKOJBS-UHFFFAOYSA-N 0.000 description 1
- FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 1
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZWJLCYURKIJHLV-UHFFFAOYSA-N 2-(2-chlorophenoxy)-N-methyl-N-[(2-methylphenyl)methyl]ethanamine Chemical compound ClC1=C(OCCN(CC2=C(C=CC=C2)C)C)C=CC=C1 ZWJLCYURKIJHLV-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000760148 Aspiculuris tetraptera Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OQMZQCZLFHARNO-UHFFFAOYSA-N Cl.CN(CCOC1=C(C=CC=C1)[N+](=O)[O-])C Chemical compound Cl.CN(CCOC1=C(C=CC=C1)[N+](=O)[O-])C OQMZQCZLFHARNO-UHFFFAOYSA-N 0.000 description 1
- 241000876447 Cooperia curticei Species 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FSDVJYLRSUQHKM-UHFFFAOYSA-N N-methyl-N-[(2-methylphenyl)methyl]-2-phenoxyethanamine Chemical compound CN(CC1=C(C=CC=C1)C)CCOC1=CC=CC=C1 FSDVJYLRSUQHKM-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- 241001126260 Nippostrongylus Species 0.000 description 1
- 241001559619 Ostertagia trifurcata Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000191771 Teladorsagia circumcincta Species 0.000 description 1
- 241000122945 Trichostrongylus axei Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 244000000053 intestinal parasite Species 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- OAWYBHWEPXYKHG-UHFFFAOYSA-N n-benzyl-2-(2-chlorophenoxy)-n-methylethanamine Chemical compound C=1C=CC=CC=1CN(C)CCOC1=CC=CC=C1Cl OAWYBHWEPXYKHG-UHFFFAOYSA-N 0.000 description 1
- DUAIQRCOSYOASH-UHFFFAOYSA-N n-benzyl-2-(2-chlorophenoxy)ethanamine Chemical compound ClC1=CC=CC=C1OCCNCC1=CC=CC=C1 DUAIQRCOSYOASH-UHFFFAOYSA-N 0.000 description 1
- WBEAMCVSKNGCJJ-UHFFFAOYSA-N n-benzyl-2-(2-methylphenoxy)ethanamine Chemical compound CC1=CC=CC=C1OCCNCC1=CC=CC=C1 WBEAMCVSKNGCJJ-UHFFFAOYSA-N 0.000 description 1
- CYFBFMUGKHDXEN-UHFFFAOYSA-N n-benzyl-n-methyl-2-(2-methylphenoxy)ethanamine Chemical compound C=1C=CC=CC=1CN(C)CCOC1=CC=CC=C1C CYFBFMUGKHDXEN-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B61—RAILWAYS
- B61B—RAILWAY SYSTEMS; EQUIPMENT THEREFOR NOT OTHERWISE PROVIDED FOR
- B61B12/00—Component parts, details or accessories not provided for in groups B61B7/00 - B61B11/00
- B61B12/02—Suspension of the load; Guiding means, e.g. wheels; Attaching traction cables
Landscapes
- Engineering & Computer Science (AREA)
- Transportation (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Laying Of Electric Cables Or Lines Outside (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG914267 | 1967-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123929B true NO123929B (member.php) | 1972-02-07 |
Family
ID=3897280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO478868A NO123929B (member.php) | 1967-12-29 | 1968-11-29 |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH499415A (member.php) |
| FR (1) | FR1599826A (member.php) |
| NO (1) | NO123929B (member.php) |
-
1968
- 1968-11-06 CH CH1654968A patent/CH499415A/fr not_active IP Right Cessation
- 1968-11-08 FR FR1599826D patent/FR1599826A/fr not_active Expired
- 1968-11-29 NO NO478868A patent/NO123929B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH499415A (fr) | 1970-11-30 |
| FR1599826A (member.php) | 1970-07-20 |
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