IL32586A - 1,3-polyhalo-2-propyl methyl and halomethyl ethers and their preparation - Google Patents
1,3-polyhalo-2-propyl methyl and halomethyl ethers and their preparationInfo
- Publication number
- IL32586A IL32586A IL32586A IL3258669A IL32586A IL 32586 A IL32586 A IL 32586A IL 32586 A IL32586 A IL 32586A IL 3258669 A IL3258669 A IL 3258669A IL 32586 A IL32586 A IL 32586A
- Authority
- IL
- Israel
- Prior art keywords
- ether
- grams
- methyl
- hexafluoro
- propyl
- Prior art date
Links
- -1 halomethyl ethers Chemical class 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 14
- 206010002091 Anaesthesia Diseases 0.000 claims description 49
- 230000037005 anaesthesia Effects 0.000 claims description 49
- 230000003444 anaesthetic effect Effects 0.000 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 239000011698 potassium fluoride Substances 0.000 claims description 13
- 235000003270 potassium fluoride Nutrition 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 11
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 claims description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- YCHHMRMFZOMLDW-UHFFFAOYSA-N chloro-[chloro(fluoro)methoxy]-fluoromethane Chemical class FC(Cl)OC(F)Cl YCHHMRMFZOMLDW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 claims description 3
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 101100069231 Caenorhabditis elegans gkow-1 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 29
- 241000282472 Canis lupus familiaris Species 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- HHYFUCXZHKDNPT-UHFFFAOYSA-N 2-(chloromethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(C(F)(F)F)OCCl HHYFUCXZHKDNPT-UHFFFAOYSA-N 0.000 description 26
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 23
- 238000004508 fractional distillation Methods 0.000 description 22
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 19
- 239000003193 general anesthetic agent Substances 0.000 description 18
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 15
- VNXYDFNVQBICRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methoxypropane Chemical compound COC(C(F)(F)F)C(F)(F)F VNXYDFNVQBICRO-UHFFFAOYSA-N 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
- 235000013350 formula milk Nutrition 0.000 description 13
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 11
- 229940035674 anesthetics Drugs 0.000 description 11
- UNIYHTKWMKXESF-UHFFFAOYSA-N 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)OC(C(F)(F)F)C(F)(F)F UNIYHTKWMKXESF-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- 125000004970 halomethyl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 9
- 235000011089 carbon dioxide Nutrition 0.000 description 9
- 238000005286 illumination Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- SGAMQLNREKTWEK-UHFFFAOYSA-N fluoro(fluoromethoxy)methane Chemical class FCOCF SGAMQLNREKTWEK-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 7
- NIWRCFDKRNOMLZ-UHFFFAOYSA-N 2-(dichloromethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(C(F)(F)F)OC(Cl)Cl NIWRCFDKRNOMLZ-UHFFFAOYSA-N 0.000 description 7
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 7
- 230000001594 aberrant effect Effects 0.000 description 7
- 206010003119 arrhythmia Diseases 0.000 description 7
- IOCGMLSHRBHNCM-UHFFFAOYSA-N difluoromethoxy(difluoro)methane Chemical compound FC(F)OC(F)F IOCGMLSHRBHNCM-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 7
- PBLGJMMEOGUSID-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)-2-[1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)propan-2-yl]oxypropane Chemical compound FCC(C(F)(F)F)(C(F)(F)F)OC(CF)(C(F)(F)F)C(F)(F)F PBLGJMMEOGUSID-UHFFFAOYSA-N 0.000 description 6
- LOSXVSQQCOVCHO-UHFFFAOYSA-N 2-[chloro(fluoro)methoxy]-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(Cl)OC(C(F)(F)F)C(F)(F)F LOSXVSQQCOVCHO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000010533 azeotropic distillation Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 239000005297 pyrex Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 5
- 231100000111 LD50 Toxicity 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229960004592 isopropanol Drugs 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CXJWJJZGJZNBRK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)propane Chemical class FC(F)(F)C(C(F)(F)F)OC(C(F)(F)F)C(F)(F)F CXJWJJZGJZNBRK-UHFFFAOYSA-N 0.000 description 4
- PBUIWAUGEWHUKT-UHFFFAOYSA-N 2-(chloromethoxy)-1,1,1,3,3-pentafluoropropane Chemical compound FC(C(C(F)F)OCCl)(F)F PBUIWAUGEWHUKT-UHFFFAOYSA-N 0.000 description 4
- LMTSEPLOXAMUKR-UHFFFAOYSA-N 2-[chloro(difluoro)methoxy]-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(C(F)(F)F)OC(F)(F)Cl LMTSEPLOXAMUKR-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- POFLFJZMEFEWRS-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(trichloromethoxy)propane Chemical class FC(F)(F)C(C(F)(F)F)OC(Cl)(Cl)Cl POFLFJZMEFEWRS-UHFFFAOYSA-N 0.000 description 3
- LLLKOOLOQRBDSS-UHFFFAOYSA-N 1,1,1,3,3-pentafluoro-2-methoxypropane Chemical compound COC(C(F)F)C(F)(F)F LLLKOOLOQRBDSS-UHFFFAOYSA-N 0.000 description 3
- WQEAIGVOMIYJBZ-UHFFFAOYSA-N 2-(bromomethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(C(F)(F)F)OCBr WQEAIGVOMIYJBZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 3
- 206010028347 Muscle twitching Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 239000003179 convulsant agent Substances 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 3
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 3
- 229960003132 halothane Drugs 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical class CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SMYMDRJWEFCCCI-UHFFFAOYSA-N trichloro(trichloromethoxy)methane Chemical class ClC(Cl)(Cl)OC(Cl)(Cl)Cl SMYMDRJWEFCCCI-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- RXHPWKPBIKICSY-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropan-2-ol Chemical compound FCC(F)(O)C(F)(F)F RXHPWKPBIKICSY-UHFFFAOYSA-N 0.000 description 2
- VXUKYFZHHFQCTQ-UHFFFAOYSA-N 1,1,1,3,3-pentafluoropropan-2-ol Chemical compound FC(F)C(O)C(F)(F)F VXUKYFZHHFQCTQ-UHFFFAOYSA-N 0.000 description 2
- OJUUDWYPNQALHZ-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(F)(F)Cl OJUUDWYPNQALHZ-UHFFFAOYSA-N 0.000 description 2
- XPWIHJOARNXKCU-UHFFFAOYSA-N 2-(dichloromethoxy)-1,1,3,3-tetrafluoropropane Chemical class FC(C(C(F)F)OC(Cl)Cl)F XPWIHJOARNXKCU-UHFFFAOYSA-N 0.000 description 2
- 206010008531 Chills Diseases 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YQEUFFBTEHNCFK-UHFFFAOYSA-N FC(C(C(F)F)OC(C(F)F)C(F)F)F Chemical class FC(C(C(F)F)OC(C(F)F)C(F)F)F YQEUFFBTEHNCFK-UHFFFAOYSA-N 0.000 description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 206010067482 No adverse event Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- LYZGJWXNOGIVQA-UHFFFAOYSA-M Thiamylal sodium Chemical compound [Na+].CCCC(C)C1(CC=C)C(=O)NC([S-])=NC1=O LYZGJWXNOGIVQA-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- CVDGHGWEHQIJTE-UHFFFAOYSA-N bromo(bromomethoxy)methane Chemical class BrCOCBr CVDGHGWEHQIJTE-UHFFFAOYSA-N 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- KGPPDNUWZNWPSI-UHFFFAOYSA-N flurotyl Chemical compound FC(F)(F)COCC(F)(F)F KGPPDNUWZNWPSI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 2
- 229960002455 methoxyflurane Drugs 0.000 description 2
- 150000005217 methyl ethers Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 231100000161 signs of toxicity Toxicity 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- WQAWXRFLNDAOON-UHFFFAOYSA-N 1,1,1,3,3-pentafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)(F)F WQAWXRFLNDAOON-UHFFFAOYSA-N 0.000 description 1
- WGOAHUOTPANWDO-UHFFFAOYSA-N 1,1,1,3-tetrafluoro-2-(1,1,1,3-tetrafluoropropan-2-yloxy)propane Chemical compound FCC(C(F)(F)F)OC(CF)C(F)(F)F WGOAHUOTPANWDO-UHFFFAOYSA-N 0.000 description 1
- CHAACYSLCZLAEN-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropan-2-one Chemical compound FCC(=O)C(F)(F)F CHAACYSLCZLAEN-UHFFFAOYSA-N 0.000 description 1
- DGVQGDJEGZBBBK-UHFFFAOYSA-N 1,1,2-trifluoro-1-methoxyethane Chemical compound COC(F)(F)CF DGVQGDJEGZBBBK-UHFFFAOYSA-N 0.000 description 1
- GPGBSJVBYLIRHH-UHFFFAOYSA-N 1,1,3,3-tetrafluoro-2-methoxypropane Chemical compound COC(C(F)F)C(F)F GPGBSJVBYLIRHH-UHFFFAOYSA-N 0.000 description 1
- OFPFGFXONBHIFF-UHFFFAOYSA-N 1,1,3,3-tetrafluoropropan-2-ol Chemical compound FC(F)C(O)C(F)F OFPFGFXONBHIFF-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical group FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- KJTNJHLLIBMHKU-UHFFFAOYSA-N 1-chloro-1,1,3,3-tetrafluoropropan-2-ol Chemical compound ClC(C(C(F)F)O)(F)F KJTNJHLLIBMHKU-UHFFFAOYSA-N 0.000 description 1
- VANKMKYWHUAISZ-UHFFFAOYSA-N 1-chloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)(F)Cl VANKMKYWHUAISZ-UHFFFAOYSA-N 0.000 description 1
- MSWVMWGCNZQPIA-UHFFFAOYSA-N 1-fluoropropan-2-one Chemical compound CC(=O)CF MSWVMWGCNZQPIA-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UCWOZTXXOVDRSK-UHFFFAOYSA-N 2-(difluoromethoxy)propane Chemical compound CC(C)OC(F)F UCWOZTXXOVDRSK-UHFFFAOYSA-N 0.000 description 1
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 1
- FAERCLVMZOAFPK-UHFFFAOYSA-N 2-chloro-1-(chloromethoxy)-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)OCCl FAERCLVMZOAFPK-UHFFFAOYSA-N 0.000 description 1
- AIFALGYICLSOQR-UHFFFAOYSA-N 3-chloro-1,1,1,2,3-pentafluoropropan-2-ol Chemical compound ClC(C(C(F)(F)F)(O)F)F AIFALGYICLSOQR-UHFFFAOYSA-N 0.000 description 1
- 241001535291 Analges Species 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- QSBKTBUCVGXQQV-UHFFFAOYSA-N FC(F)C(F)(F)OCCl Chemical compound FC(F)C(F)(F)OCCl QSBKTBUCVGXQQV-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229940095672 calcium sulfate Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- MSZJNXZCQSENHN-UHFFFAOYSA-N chloro-[chloro(difluoro)methoxy]-difluoromethane Chemical class FC(F)(Cl)OC(F)(F)Cl MSZJNXZCQSENHN-UHFFFAOYSA-N 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 229950000929 flurotyl Drugs 0.000 description 1
- DLEGDLSLRSOURQ-UHFFFAOYSA-N fluroxene Chemical compound FC(F)(F)COC=C DLEGDLSLRSOURQ-UHFFFAOYSA-N 0.000 description 1
- 229950010045 fluroxene Drugs 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229940005494 general anesthetics Drugs 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 231100000812 repeated exposure Toxicity 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
- 229940032712 succinylcholine Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- WZEOZJQLTRFNCU-UHFFFAOYSA-N trifluoro(trifluoromethoxy)methane Chemical class FC(F)(F)OC(F)(F)F WZEOZJQLTRFNCU-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77136568A | 1968-10-28 | 1968-10-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32586A0 IL32586A0 (en) | 1969-09-25 |
| IL32586A true IL32586A (en) | 1973-11-28 |
Family
ID=25091570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32586A IL32586A (en) | 1968-10-28 | 1969-07-09 | 1,3-polyhalo-2-propyl methyl and halomethyl ethers and their preparation |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS5228772B1 (enrdf_load_stackoverflow) |
| BE (1) | BE735828A (enrdf_load_stackoverflow) |
| CH (1) | CH539008A (enrdf_load_stackoverflow) |
| DE (1) | DE1954268C3 (enrdf_load_stackoverflow) |
| DK (1) | DK127971B (enrdf_load_stackoverflow) |
| FR (1) | FR2021695B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1250928A (enrdf_load_stackoverflow) |
| IL (1) | IL32586A (enrdf_load_stackoverflow) |
| NL (1) | NL165448C (enrdf_load_stackoverflow) |
| SE (2) | SE397971B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883664A (en) * | 1973-01-29 | 1975-05-13 | Airco Inc | Hexafluoro-t-butyl difluoromethyl ether as an inhalation anesthetic |
| US3949005A (en) * | 1974-05-09 | 1976-04-06 | Airco, Inc. | Hexafluoro-t-butyl-difluoromethyl ether as an inhalation anesthetic |
| US6100434A (en) * | 1999-03-26 | 2000-08-08 | Abbott Laboratories | Method for synthesizing sevoflurane and an intermediate thereof |
| US6303831B1 (en) * | 2000-06-01 | 2001-10-16 | Abbott Laboratories | Synthetic method for fluoromethylation of halogenated alcohols |
| US6271422B1 (en) * | 2000-06-01 | 2001-08-07 | Abbott Laboratories | Method for fluoromethylation of alcohols via halogenative decarboxylation |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
| JP5021745B2 (ja) | 2006-09-29 | 2012-09-12 | クリスタリア プロデュトス キミコス ファーマシューティコス リミターダ | フルオロメチル２，２，２−トリフロオロ−１−（トリフルオロメチル）エチルエーテルの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352928A (en) * | 1965-09-14 | 1967-11-14 | Allied Chem | Fluorinated alcohol and ether derivatives thereof |
| US3346448A (en) * | 1965-09-14 | 1967-10-10 | Allied Chem | Hexafluoroisopropyl ethers as anesthetics |
-
1969
- 1969-07-09 GB GB1250928D patent/GB1250928A/en not_active Expired
- 1969-07-09 BE BE735828D patent/BE735828A/xx not_active IP Right Cessation
- 1969-07-09 IL IL32586A patent/IL32586A/en unknown
- 1969-08-28 JP JP44067646A patent/JPS5228772B1/ja active Pending
- 1969-10-24 FR FR696936487A patent/FR2021695B1/fr not_active Expired
- 1969-10-24 NL NL6916076.A patent/NL165448C/xx not_active IP Right Cessation
- 1969-10-27 SE SE6914679A patent/SE397971B/xx unknown
- 1969-10-28 DK DK568469AA patent/DK127971B/da not_active IP Right Cessation
- 1969-10-28 CH CH1603169A patent/CH539008A/de not_active IP Right Cessation
- 1969-10-28 DE DE1954268A patent/DE1954268C3/de not_active Expired
-
1976
- 1976-05-07 SE SE7605232A patent/SE445550B/xx not_active IP Right Cessation
- 1976-07-15 JP JP8493476A patent/JPS5344443B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE735828A (enrdf_load_stackoverflow) | 1969-12-16 |
| DE1954268B2 (de) | 1978-10-19 |
| FR2021695B1 (enrdf_load_stackoverflow) | 1973-06-08 |
| GB1250928A (enrdf_load_stackoverflow) | 1971-10-27 |
| NL165448B (nl) | 1980-11-17 |
| SE445550B (sv) | 1986-06-30 |
| SE7605232L (sv) | 1976-05-07 |
| DE1954268A1 (de) | 1970-05-27 |
| NL6916076A (enrdf_load_stackoverflow) | 1970-05-01 |
| JPS5344443B1 (enrdf_load_stackoverflow) | 1978-11-29 |
| IL32586A0 (en) | 1969-09-25 |
| DE1954268C3 (de) | 1979-06-13 |
| NL165448C (nl) | 1981-04-15 |
| CH539008A (de) | 1973-07-15 |
| FR2021695A1 (enrdf_load_stackoverflow) | 1970-07-24 |
| DK127971B (da) | 1974-02-11 |
| SE397971B (sv) | 1977-11-28 |
| JPS5228772B1 (enrdf_load_stackoverflow) | 1977-07-28 |
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