BE537756A - - Google Patents
Info
- Publication number
- BE537756A BE537756A BE537756DA BE537756A BE 537756 A BE537756 A BE 537756A BE 537756D A BE537756D A BE 537756DA BE 537756 A BE537756 A BE 537756A
- Authority
- BE
- Belgium
- Prior art keywords
- pentane
- phthalimido
- ethanol
- aminophenoxy
- filtered
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 160
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 136
- 238000002844 melting Methods 0.000 claims 52
- 230000008018 melting Effects 0.000 claims 52
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 36
- 239000000203 mixture Substances 0.000 claims 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 34
- 150000003254 radicals Chemical class 0.000 claims 28
- 238000001953 recrystallisation Methods 0.000 claims 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 22
- 239000000047 product Substances 0.000 claims 21
- 239000000243 solution Substances 0.000 claims 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- 239000007787 solid Substances 0.000 claims 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- 239000000155 melt Substances 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 11
- 238000010992 reflux Methods 0.000 claims 10
- 238000009835 boiling Methods 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 7
- 239000000706 filtrate Substances 0.000 claims 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 7
- 239000003208 petroleum Substances 0.000 claims 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 6
- 238000002425 crystallisation Methods 0.000 claims 6
- 230000008025 crystallization Effects 0.000 claims 6
- QKVHAKICMNABGB-UHFFFAOYSA-N 2-(5-bromopentyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCBr)C(=O)C2=C1 QKVHAKICMNABGB-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 238000004821 distillation Methods 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 4
- 229910003446 platinum oxide Inorganic materials 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 229910052708 sodium Inorganic materials 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- 125000001302 tertiary amino group Chemical group 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 150000002828 nitro derivatives Chemical class 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 claims 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- RIUQVLLXSSNFPD-UHFFFAOYSA-N CCCCC(OC(C=C1)=CC=C1[N+]([O-])=O)Br Chemical compound CCCCC(OC(C=C1)=CC=C1[N+]([O-])=O)Br RIUQVLLXSSNFPD-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 claims 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- LPKYKQBWTIDVHN-UHFFFAOYSA-N n-(4-hydroxyphenyl)-n-methylformamide Chemical compound O=CN(C)C1=CC=C(O)C=C1 LPKYKQBWTIDVHN-UHFFFAOYSA-N 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims 2
- 238000000197 pyrolysis Methods 0.000 claims 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims 2
- 229940081974 saccharin Drugs 0.000 claims 2
- 235000019204 saccharin Nutrition 0.000 claims 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- 238000001665 trituration Methods 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- RZCNIOWAJWZKDD-UHFFFAOYSA-N (4-hydroxyphenyl)-trimethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=C(O)C=C1 RZCNIOWAJWZKDD-UHFFFAOYSA-N 0.000 claims 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 claims 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 claims 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 claims 1
- XHUZBWUNHJZIHE-UHFFFAOYSA-N 2-(5-phenoxypentyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCCOC1=CC=CC=C1 XHUZBWUNHJZIHE-UHFFFAOYSA-N 0.000 claims 1
- OAZFTIPKNPTDIO-UHFFFAOYSA-N 2-(6-bromohexyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCCBr)C(=O)C2=C1 OAZFTIPKNPTDIO-UHFFFAOYSA-N 0.000 claims 1
- ARGIXEIFTPBJRC-UHFFFAOYSA-N 2-(7-bromoheptyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCCCBr)C(=O)C2=C1 ARGIXEIFTPBJRC-UHFFFAOYSA-N 0.000 claims 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 229940093475 2-ethoxyethanol Drugs 0.000 claims 1
- SRFRJCMUBGZTAP-UHFFFAOYSA-N 2-pentylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCC)C(=O)C2=C1 SRFRJCMUBGZTAP-UHFFFAOYSA-N 0.000 claims 1
- BVTLIIQDQAUXOI-UHFFFAOYSA-N 4-(benzylideneamino)phenol Chemical compound C1=CC(O)=CC=C1N=CC1=CC=CC=C1 BVTLIIQDQAUXOI-UHFFFAOYSA-N 0.000 claims 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 claims 1
- CBDLLOONIRUKRB-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)pentyl methanesulfonate Chemical compound C1=CC=C2C(=O)N(CCCCCOS(=O)(=O)C)C(=O)C2=C1 CBDLLOONIRUKRB-UHFFFAOYSA-N 0.000 claims 1
- QTNVULGCBFTXBM-UHFFFAOYSA-N 5-methylsulfonyloxypentyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCOS(C)(=O)=O QTNVULGCBFTXBM-UHFFFAOYSA-N 0.000 claims 1
- 241000238876 Acari Species 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- FAUCCKXDWBWYGL-UHFFFAOYSA-N NC=1C=C2C(C(=O)N(C2=O)C(CCCC)OC2=CC=CC=C2)=CC=1 Chemical compound NC=1C=C2C(C(=O)N(C2=O)C(CCCC)OC2=CC=CC=C2)=CC=1 FAUCCKXDWBWYGL-UHFFFAOYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- GIIGAFADHXYOPM-UHFFFAOYSA-N amphotalide Chemical compound C1=CC(N)=CC=C1OCCCCCN1C(=O)C2=CC=CC=C2C1=O GIIGAFADHXYOPM-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 159000000007 calcium salts Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 125000006011 chloroethoxy group Chemical group 0.000 claims 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 150000001470 diamides Chemical class 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 239000011872 intimate mixture Substances 0.000 claims 1
- ADDQUOLYROTOKS-UHFFFAOYSA-N iodomethanol Chemical compound OCI ADDQUOLYROTOKS-UHFFFAOYSA-N 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 claims 1
- UMNSMBWAESLVOC-UHFFFAOYSA-N n-pentylaniline Chemical compound CCCCCNC1=CC=CC=C1 UMNSMBWAESLVOC-UHFFFAOYSA-N 0.000 claims 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000004409 schistosomiasis Diseases 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims 1
- XUIVKWAWICCWIQ-UHFFFAOYSA-M sodium;formaldehyde;hydrogen sulfite Chemical compound [Na+].O=C.OS([O-])=O XUIVKWAWICCWIQ-UHFFFAOYSA-M 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000011269 tar Substances 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 150000004684 trihydrates Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000004690 nonahydrates Chemical class 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE537756A true BE537756A (enExample) |
Family
ID=168017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE537756D BE537756A (enExample) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE537756A (enExample) |
-
0
- BE BE537756D patent/BE537756A/fr unknown
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