SU432722A3 - - Google Patents
Info
- Publication number
- SU432722A3 SU432722A3 SU1813601A SU1813601A SU432722A3 SU 432722 A3 SU432722 A3 SU 432722A3 SU 1813601 A SU1813601 A SU 1813601A SU 1813601 A SU1813601 A SU 1813601A SU 432722 A3 SU432722 A3 SU 432722A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloride
- nitrothiazole
- carboxylic acid
- treated
- methylene chloride
- Prior art date
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- JNCIUFLBNBFHHF-UHFFFAOYSA-N 5-nitro-1,3-thiazole-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CN=C(C(Cl)=O)S1 JNCIUFLBNBFHHF-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- -1 phenoxyl residue Chemical group 0.000 description 6
- KNAAFBMBMBMZHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole-2-carboxylic acid Chemical class OC(=O)C1=NC=C([N+]([O-])=O)S1 KNAAFBMBMBMZHI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- XADDQIHVHRSTNY-UHFFFAOYSA-N (3,4-dimethylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C1=C(C)C(C)=CC=C1C(=O)C1=NC=C([N+]([O-])=O)S1 XADDQIHVHRSTNY-UHFFFAOYSA-N 0.000 description 1
- PPYKSXUJXRHLTL-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound ClC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1C PPYKSXUJXRHLTL-UHFFFAOYSA-N 0.000 description 1
- IZGQKBQXQIBSDR-UHFFFAOYSA-N (3-fluoro-4-methoxyphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound FC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1OC IZGQKBQXQIBSDR-UHFFFAOYSA-N 0.000 description 1
- OLQUVEQZDQOKMC-UHFFFAOYSA-N (4-butoxyphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C(CCC)OC1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 OLQUVEQZDQOKMC-UHFFFAOYSA-N 0.000 description 1
- SHXIJVVHRANJPR-UHFFFAOYSA-N (4-butylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C(CCC)C1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 SHXIJVVHRANJPR-UHFFFAOYSA-N 0.000 description 1
- UBEUCJVHCJWINI-UHFFFAOYSA-N (4-fluorophenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=C(F)C=C1 UBEUCJVHCJWINI-UHFFFAOYSA-N 0.000 description 1
- KMGHJIANBCQKGH-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound CC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1OC KMGHJIANBCQKGH-UHFFFAOYSA-N 0.000 description 1
- DZOXUSREIVLBID-UHFFFAOYSA-N (4-methylsulfanylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound CSC1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 DZOXUSREIVLBID-UHFFFAOYSA-N 0.000 description 1
- GSRLEXHGKSSJHH-UHFFFAOYSA-N (5-methylfuran-2-yl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound O1C(C)=CC=C1C(=O)C1=NC=C([N+]([O-])=O)S1 GSRLEXHGKSSJHH-UHFFFAOYSA-N 0.000 description 1
- UAXONMKTPVEOLZ-UHFFFAOYSA-N (5-nitro-1,3-thiazol-2-yl)-(4-phenoxyphenyl)methanone Chemical compound O(C1=CC=CC=C1)C1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 UAXONMKTPVEOLZ-UHFFFAOYSA-N 0.000 description 1
- GEJHTCFKDKDBIN-UHFFFAOYSA-N (5-nitro-1,3-thiazol-2-yl)-phenylmethanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=CC=C1 GEJHTCFKDKDBIN-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- JIXDOBAQOWOUPA-UHFFFAOYSA-N 1-fluoro-2-methoxybenzene Chemical compound COC1=CC=CC=C1F JIXDOBAQOWOUPA-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- FMYPRMYBSKSMMU-UHFFFAOYSA-N furan-2-yl-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=CO1 FMYPRMYBSKSMMU-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XXPDBLUZJRXNNZ-UHFFFAOYSA-N promethazine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 XXPDBLUZJRXNNZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/58—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
- Fodder In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2204364A DE2204364A1 (de) | 1972-01-27 | 1972-01-27 | 2-acyl-5-nitrothiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU432722A3 true SU432722A3 (enExample) | 1974-06-15 |
Family
ID=5834503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1813601A SU432722A3 (enExample) | 1972-01-27 | 1972-07-21 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3830826A (enExample) |
| JP (1) | JPS4885571A (enExample) |
| AR (1) | AR192792A1 (enExample) |
| AT (1) | AT315166B (enExample) |
| AU (1) | AU468236B2 (enExample) |
| BE (1) | BE785368A (enExample) |
| CA (1) | CA987326A (enExample) |
| CH (1) | CH569000A5 (enExample) |
| DD (1) | DD100719A5 (enExample) |
| DE (1) | DE2204364A1 (enExample) |
| EG (1) | EG10728A (enExample) |
| ES (2) | ES405437A1 (enExample) |
| FR (1) | FR2169018B1 (enExample) |
| GB (1) | GB1400604A (enExample) |
| HU (1) | HU162904B (enExample) |
| IL (1) | IL39838A (enExample) |
| NL (1) | NL7208801A (enExample) |
| SE (1) | SE377939B (enExample) |
| SU (1) | SU432722A3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006241A (en) * | 1972-06-23 | 1977-02-01 | Schering Aktiengesellschaft | Certain halothien-2-yl 5-nitrothiazol-2-yl ketones and fungicidal composition |
| US4269985A (en) * | 1980-07-30 | 1981-05-26 | Eastman Kodak Company | Process for the preparation of 2-amino-5-nitrothiazole |
-
1972
- 1972-01-27 DE DE2204364A patent/DE2204364A1/de active Pending
- 1972-04-27 CH CH626872A patent/CH569000A5/xx not_active IP Right Cessation
- 1972-06-01 DD DD163353A patent/DD100719A5/xx unknown
- 1972-06-14 AR AR242556A patent/AR192792A1/es active
- 1972-06-15 AT AT515772A patent/AT315166B/de not_active IP Right Cessation
- 1972-06-21 EG EG274/72A patent/EG10728A/xx active
- 1972-06-21 SE SE7208197A patent/SE377939B/xx unknown
- 1972-06-22 HU HUSC400A patent/HU162904B/hu unknown
- 1972-06-23 FR FR7222737A patent/FR2169018B1/fr not_active Expired
- 1972-06-23 BE BE785368A patent/BE785368A/xx unknown
- 1972-06-23 US US00265462A patent/US3830826A/en not_active Expired - Lifetime
- 1972-06-26 NL NL7208801A patent/NL7208801A/xx unknown
- 1972-06-26 GB GB2983072A patent/GB1400604A/en not_active Expired
- 1972-07-06 IL IL39838A patent/IL39838A/xx unknown
- 1972-07-21 SU SU1813601A patent/SU432722A3/ru active
- 1972-08-02 ES ES405437A patent/ES405437A1/es not_active Expired
- 1972-08-02 ES ES405438A patent/ES405438A1/es not_active Expired
- 1972-08-18 CA CA149,736A patent/CA987326A/en not_active Expired
- 1972-08-18 AU AU45753/72A patent/AU468236B2/en not_active Expired
- 1972-08-21 JP JP47083552A patent/JPS4885571A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EG10728A (en) | 1976-05-31 |
| JPS4885571A (enExample) | 1973-11-13 |
| AU468236B2 (en) | 1976-01-08 |
| HU162904B (enExample) | 1973-04-28 |
| US3830826A (en) | 1974-08-20 |
| SE377939B (enExample) | 1975-08-04 |
| NL7208801A (enExample) | 1973-07-31 |
| GB1400604A (en) | 1975-07-16 |
| FR2169018B1 (enExample) | 1975-06-20 |
| ES405438A1 (es) | 1975-07-16 |
| IL39838A0 (en) | 1972-09-28 |
| CA987326A (en) | 1976-04-13 |
| FR2169018A1 (enExample) | 1973-09-07 |
| IL39838A (en) | 1975-05-22 |
| AT315166B (de) | 1974-05-10 |
| AU4575372A (en) | 1974-02-21 |
| ES405437A1 (es) | 1975-09-01 |
| BE785368A (fr) | 1972-12-27 |
| DE2204364A1 (de) | 1973-08-02 |
| CH569000A5 (enExample) | 1975-11-14 |
| AR192792A1 (es) | 1973-03-14 |
| DD100719A5 (enExample) | 1973-10-05 |
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